JP6050291B2 - Method for producing solanone and synthetic intermediate thereof - Google Patents

Description

  The present invention relates to a novel process for producing solanone useful for a perfume compound and the like, and a novel intermediate useful for producing solanone.

  Solanone was isolated as an important aroma component of tobacco in 1965 as an oxidative degradation product of cembranoid, which is a diterpene contained in tobacco plants, and its structure was determined by organic synthesis (Non-patent Document 1). It is a ketone having 13 carbon atoms having a double bond conjugated in the molecule, and an excellent effect on tobacco aroma, particularly taste, has been confirmed, and many synthetic methods have been proposed.

  A method of synthesizing from a nitrile in which conjugated double bonds are introduced by Wittig reaction using non-patent literature 1 using isovaleraldehyde and acrylonitrile as a raw material is simple as a laboratory-level synthesis method. However, industrial production has difficulties such as exchanging the solvent from diethyl ether to benzene during the reaction with the Grignard reagent for converting cyano group to methyl ketone. Attempts to introduce conjugated double bonds by the dehydration method have also been proposed, but there is a problem that the conjugated double bonds move during the dehydration reaction to produce isosolanone. Moreover, there exists a problem which uses methyl lithium with high ignitability in conversion from a cyano group to methyl ketone (patent document 1). A method of synthesizing from ethyl isovalerate by a similar method has also been proposed (Non-patent Document 2).

  In addition, a synthesis method using a rearrangement reaction has also been proposed, but there is a problem that isosolanone in which a conjugated double bond has moved is generated (Patent Document 2).

  On the other hand, attempts have been made to use natural raw material limonene as a raw material. As a photo-oxidation reaction and a key reaction, a method via an acetylene intermediate (Non-patent Document 3) and a method of synthesizing solanone from ketoaldehyde obtained by ozone oxidation of paramentene have been proposed (Patent Document 3). And Non-Patent Document 4). However, protection and deprotection steps are involved, and high temperature conditions are required for the introduction of conjugated double bonds. Furthermore, a method for synthesizing solanone from ketoacetal obtained by ozonolysis, reduction, and acetalization of paramentene has also been proposed (Patent Document 4). However, since many processes are required, it is not suitable for industrialization.

  A method for producing a solanone intermediate without using ozone oxidation by selecting limonene oxide as a raw material has also been proposed (Patent Document 5). Although these methods have an advantage that a natural type optically active solanone can be obtained, they require many steps and are not a method for industrially supplying a large amount of solanone.

  A production method that satisfies both the construction of an unstable conjugated double bond and the simple conversion to methyl ketone has not been developed. Thus, no production method has been proposed for synthesizing a large amount of solanone, which is important as a perfume compound, with a small number of steps and a safe technique. In particular, development of a production method that satisfies both the construction of an unstable conjugated double bond and the simple conversion to methyl ketone is desired.

U.S. Pat.No. 4,420,083 U.S. Pat. No. 4,433,695 JP-A-64-66137 Japanese Patent Publication No. 7-100675 JP 2013-1695 A

The Journal of Organic Chemistry (1965), 30 (9), 2918-2921. Bulletin of the Korean Chemical Society (1993), 14 (5), 639-641. Journal of the Chemical Society, Chemical Communications (1981), 951-952. Synthesis, 1994 (7), 692-694.

  The object of the present invention is to provide a method for industrially producing a large amount of solanone, which is important as a perfume compound, in a small number of steps and in a safe manner.

  As a result of intensive studies to solve the above problems, the present inventors have made Michael addition reaction of N- (3-methyl-1-butenyl) piperidine to 4-acryloylmorpholine, followed by acid hydrolysis. A novel aldehyde was formed, and this aldehyde was subjected to Wittig reaction to form a new morpholine amide, which was further reacted with a Grignard reagent to find a method for producing solanone in a large amount by an industrial technique, and the present invention was found. It came to be completed.

  The novel morpholine amide compound represented by the formula (1) can be easily derived into methyl ketone while retaining the conjugated double bond in the molecule, and is a key for producing various terpenes such as solanone. It is a compound that can be said to be a synthetic intermediate. In addition, as far as the present inventors know, this compound is also a novel compound not described in any literature.

  Accordingly, the present invention provides the following compounds that are such synthetic intermediates, methods for producing the compounds, methods for producing solanone from the compounds, and compounds that are novel precursors for producing the intermediates. .

[1] A compound represented by the following formula (1).

[2] A method for producing a compound represented by the formula (1) according to [1],
Following formula (4)

N- (3-methyl-1-butenyl) piperidine represented by the following formula (5)

And 4-acryloylmorpholine represented by the following formula (6):

Obtaining a compound represented by:
The compound represented by the formula (6) thus obtained was added to the following formula (7)

(Wherein X represents a halogen atom and Ph represents a phenyl group), which comprises a step of causing a Wittig reaction with a halogenated 2-methyl-2-propenyltriphenylphosphonium.

[3] The following formula (8)

A method for producing solanone represented by:
[1] A production method comprising a step of reacting a Grignard reagent capable of converting a morpholinamide moiety of a compound represented by the formula (1) according to [1] into methylcarbonyl.

[4] A compound represented by the following formula (6).

  INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a method capable of producing a large amount of solanone useful as a perfume compound by an industrial technique in a short process compared to the conventional production method, and various terpenes including solanone. It is possible to provide a novel synthetic intermediate that can be effectively produced.

  Hereinafter, the present invention will be described in more detail.

  One aspect of the present invention is the following formula (1):

And a novel compound important as a synthetic intermediate for producing various terpenes including solanone. Such terpenes other than solanone include, but are not limited to, isosolanone (5-isopropyl-8-methyl-5,7-nonadien-2-one), which may constitute other tobacco fragrance compositions, Norsolanadione (5-isopropyl-6-nonene-2,8-dione), solanol (5-isopropyl-8-methyl-6,8-nonadien-2-ol), 8-oxo-5-isopropyl-2-methyl- 3-nonen-2-ol, 8-oxo-5-isopropyl-2-methyl-4-nonen-2-ol, 8-oxo-5-isopropyl-3-nonen-2-ol, 8-isopropyl-11- Methyl-9,11-dodecadien-5-one, 7-isopropyl-2,10-dimethyl-8,10-undecadien-4-one, 7-isopropyl-3 , And the like 10-dimethyl-8,10-undecadiene-4-one.

  N- (3-methyl-1-butenyl) piperidine represented by the above formula (4) used as a starting material of the present invention can be prepared by a conventionally known method. For example, it is represented by the following reaction formula. As described above, it can be produced by dropping isovaleraldehyde from piperidine as a raw material.

  Used to produce N- (3-methyl-1-butenyl) piperidine represented by formula (4) from piperidine represented by formula (2) and isovaleraldehyde represented by formula (3) Isovaleraldehyde can be used in an amount of 0.2 mol to 2 mol, preferably 0.8 to 1.2 mol, relative to 1 mol of piperidine.

  In the above reaction formula, potassium carbonate used for producing N- (3-methyl-1-butenyl) piperidine represented by the formula (4) is 0.1 to 0 per 1 mol of piperidine. By using 0.5 mol, preferably 0.2 to 0.4 mol, the yield of the compound of the formula (4) can be increased.

  In order to produce N- (3-methyl-1-butenyl) piperidine represented by formula (4) from piperidine represented by formula (2) and isovaleraldehyde represented by formula (3), piperidine is used in advance. And potassium carbonate are charged into a reaction vessel, and isovaleraldehyde is preferably added dropwise to the reaction vessel in a nitrogen atmosphere and at a low temperature. The reaction temperature is preferably in the range of 0 ° C to 30 ° C.

  The aldehyde represented by the following formula (6) is a novel compound not described in the conventional literature, and as shown by the following reaction formula, N- (3-methyl-) represented by the following formula (4) 1-butenyl) piperidine can be produced by Michael addition reaction with 4-acryloylmorpholine represented by the following formula (5), followed by acid hydrolysis. Therefore, the compound represented by the formula (6) is also an important synthetic intermediate of the compound represented by the formula (1) according to the present invention, and is provided as one embodiment of the present invention.

Since 4-acryloylmorpholine represented by the formula (5) is a polymer raw material, it can be obtained industrially at low cost. For example, 4-acryloyl morpholine (manufactured by Tokyo Chemical Industry Co., Ltd.), 4-acryloyl morpholine (manufactured by Wako Pure Chemical Industries, Ltd.), 4-acryloyl morpholine (manufactured by Kojin Film & Chemical Co., Ltd.) and the like can be mentioned.

  The compound of formula (6) can be produced by subjecting the compound represented by formula (4) and the compound represented by formula (5) to a Michael addition reaction and then acid hydrolysis. The compound represented by the formula (5) used in this case is used in an amount of 0.5 to 3.0 mol, more preferably 1.0 to 2.0 mol, with respect to 1 mol of the compound represented by the formula (4). It is preferable to do.

  The reaction is preferably carried out with stirring under a nitrogen atmosphere. The reaction is preferably performed at a heating temperature of 100 ° C. to 150 ° C., more preferably 120 ° C. to 140 ° C., and a heating time of 30 minutes to 12 hours, preferably 2 hours to 6 hours.

  In the reaction formula, the acid used in the acid hydrolysis is not particularly limited as long as it can be hydrolyzed, but is preferably a salt of a strong acid and a weak base. Examples thereof include ammonium chloride and ammonium sulfate.

  The morpholine amide compound represented by the following formula (1) is a novel compound not described in the conventional literature, and as shown by the following reaction formula, the aldehyde represented by the following formula (6) It can be produced by a Wittig reaction in the presence of 2-methyl-2-propenyltriphenylphosphonium halide represented by (7) and an alkali hydride.

  (Wherein X represents a halogen atom and Ph represents a phenyl group)

  The compound represented by the formula (7), which is a Wittig reagent for the Wittig reaction of the above formula, can be obtained by reacting triphenylphosphine and 2-methyl-2-propenyl halide. The Wittig reagent is particularly preferably 2-methyl-2-propenyltriphenylphosphonium chloride, 2-methyl-2-propenyltriphenylphosphonium bromide, or the like.

  The Wittig reagent represented by the formula (7) used in the reaction formula is 0.5 to 5.0 mol, preferably 1.0 to 3 with respect to 1 mol of the aldehyde represented by the formula (6). By using 0.0 mol, the Wittig reaction is promoted.

  Examples of the alkali hydride used when performing the Wittig reaction of the above formula include sodium hydride, potassium hydride, calcium hydride, and magnesium hydride. The alkali hydride is used in an amount of 0.2 to 5.0 moles, preferably 1.0 to 2.0 moles per mole of the aldehyde represented by the formula (6). Promoted.

  Examples of the solvent used for the Wittig reaction of the above formula include ether ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, cyclopentyl methyl ether, 2-methylpropyl methyl ether, 1,4-dioxane, and tetrahydrofuran. Among them, tetrahydrofuran is particularly preferable.

  The reaction time for carrying out the Wittig reaction of the above formula can be 30 minutes to 6 hours, preferably 2 to 4 hours. The reaction temperature for carrying out the Wittig reaction is 40 ° C. to 90 ° C., preferably 55 ° C. ˜75 ° C. can be mentioned.

  As shown in the following reaction formula, the compound represented by the following formula (1) is subjected to a Grignard reaction using a methylmagnesium halide capable of converting the morpholinamide moiety in the formula (1) into methylcarbonyl. A solanone represented by the formula (8) can be produced.

  (Wherein X 'represents a halogen atom)

  X ′ in the reaction formula represents a halogen atom, and examples thereof include chlorine, bromine, iodine and the like. The amount of Grignard reagent represented by MeMgX ′ is preferably 0.2 to 5.0 mol, more preferably 1.0 to 2.0 mol, relative to 1 mol of the compound represented by formula (1). Is more preferable.

  Examples of the solvent used in producing the solanone represented by the formula (8) by the Grignard reaction from the morpholine amide compound represented by the formula (1) include diethyl ether, diisopropyl ether, methyl t-butyl ether, cyclopentyl. Mention may be made of ether solvents such as methyl ether, 2-methylpropyl methyl ether, 1,4-dioxane and tetrahydrofuran, with tetrahydrofuran being particularly preferred.

  In order to produce the solanone represented by the formula (8) from the morpholine amide compound represented by the formula (1) by a Grignard reaction, the compound of the formula (1) and a solvent are charged in a reaction vessel in advance, It is preferable to add the Grignard reagent dropwise to the reaction vessel at a low temperature. Moreover, as for the temperature in that case, it is desirable not to raise the temperature in a reaction system, and -20 degreeC-20 degreeC can be illustrated.

  The compounds represented by the formula (1), formula (4), formula (6) and formula (8) obtained by the above reaction can be purified by an ordinary purification method such as distillation or silica gel chromatography. .

  Through the steps described above, high-quality solanone represented by the formula (8) having a chemical purity of 90% or more can be produced.

  The solanone represented by the formula (8) thus obtained is, for example, a cereal product, a rice product, a tapioca product, a biscuit, a pastry, a bakery product, a confectionery, a dessert, a gum, a chewing gum, a chocolate, an ice, a honey, Molasses, yeast products, baking powder, salt and spices, mustard, edible vinegar, sauces, tobacco, processed foods, cooked fruit and vegetable products, meat and meat products, jelly, jam, fruit sauces, egg products, milk and dairy products , Cheese, butter and butter substitute products, milk substitutes, soy products, edible oils and fats, pharmaceuticals, beverages, alcoholic beverages, beer, soft drinks, mineral water, non-alcoholic beverages, fruit beverages, fruit juice, coffee, tea, cocoa, edible Extract, plant extract, meat extract, seasoning, sweetener, nutritional supplement, gelatin, medicinal and Unmedicated gums, tablets, lozenges, can be provided as a flavor to be added to foods containing food directly or Soranon such as drop, syrup.

  The above flavors are well known food additives such as solvents, binders, diluents, disintegrants, lubricants, flavor additives, colorants, preservatives, antioxidants, emulsifiers, stabilizers, flavors. An enhancer, sweetener, and the like may be included.

  The flavor may also be added to the food product in any suitable form, for example as a liquid, as a paste, or in an encapsulated form bound or coated on a carrier / particle, or as a powder.

  The solanone represented by the formula (8) varies depending on the target fragrance, the use of the flavor, etc., as a blending amount with respect to the flavor, but generally 0.01 to 20% by mass in the flavor, preferably 0.1-10 mass% can be mix | blended.

  Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these.

Reference Example 1: Synthesis of N- (3-methyl-1-butenyl) piperidine (compound of formula (4)) Potassium carbonate (420.0 g, 3.04 mol, 35.3 mol%) in a 3 L four-necked flask , Piperidine (874.0 g, 10.3 mol, 1.2 eq.) Was charged, and the mixture was stirred under a nitrogen atmosphere and ice water cooling. When the internal temperature reached 10 ° C, isovaleraldehyde (741.0 g, 8.60 mol) was added dropwise for 2.5 hours (internal temperature 25 ° C or lower). After dropping, the mixture was stirred at room temperature for 2.5 hours, and then filtered, dried and concentrated to obtain 1608.2 g of a crude product. This crude product was purified by distillation under reduced pressure to obtain 1170.9 g of N- (3-methyl-1-butenyl) piperidine represented by the above formula (4) (yield 88.8%).

  Further, as a result of gas chromatographic analysis of N- (3-methyl-1-butenyl) piperidine obtained in Reference Example 1, the chemical purity was 99.1% (analysis conditions, column: TC-1701). (30 m × 0.53 mm), temperature rising conditions: 100 ° C. to 260 ° C., holding for 2 min at 100 ° C., 20.0 ° C./min temperature rising, carrier gas: nitrogen, linear velocity: 60 cm / sec, holding time: 4.7 min).

Example 1 Synthesis of Aldehyde (Compound of Formula (6)) N- (3-methyl-1-butenyl) piperidine (333.5 g) represented by Formula (4) in a 2 L four-necked flask was obtained. 18 mol) and 4-acryloylmorpholine (461.8 g, 3.27 mol, 1.5 eq.) Were charged, and the mixture was heated and stirred at 130 ° C. for 4 hours under a nitrogen atmosphere. Thereafter, the reaction solution was cooled to room temperature, and the reaction solution and ethyl acetate (500 g) were added to an 18 L vessel containing 20% aqueous ammonium chloride (5000 g). After stirring overnight, 10% sulfuric acid (1250 g) was added to adjust the pH to a range of 1 to 2, the aqueous layer was saturated with sodium chloride (1400 g), and then the organic layer was separated. Thereafter, the aqueous layer was extracted with ethyl acetate (500 g × twice). The organic layers were combined, washed with 20% brine (500 g) and 15% aqueous sodium carbonate solution (500 g) in this order, then dried and concentrated, and the crude purified product of aldehyde represented by the above formula (6) was 438. 5 g was obtained (yield of crude product: 88.5%).

In addition, as a result of gas chromatographic analysis of the crude purified product of aldehyde represented by the above formula (6) obtained in Example 1, the chemical purity was 95.1% (analysis conditions, column: TC -1701 (30 m × 0.53 mm), temperature rising condition: 100 ° C. to 260 ° C., holding at 100 ° C. for 2 min, 20.0 ° C./min heating, carrier gas: nitrogen, linear velocity: 60 cm / sec, holding Time: 10.8 min).

Physical property data of formula (6) aldehyde
¹ H-NMR (400 MHz, CDCl ₃ ): δ ppm 0.96 (d, J = 6.8 Hz, 3H), 1.00 (d, J = 6.8 Hz, 3H), 1.77-1.94 ( m, 2H), 2.02-2.11 (m, 1H), 2.13-2.22 (m, 2H), 2.31-2.39 (m, 1H), 3.42-3. 45 (m, 2H), 3.54-3.61 (m, 2H), 3.62-3.66 (m, 4H), 9.63 (d, J = 2.4 Hz, 3H)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ ppm 19.4, 20.3, 20.8, 28.4, 30.9, 41.9, 45.8, 57.7, 66.6, 66. 8, 170.9, 205.4
MS (m / z): 41, 43, 55, 56, 57, 69, 70, 86, 87, 88, 99, 114, 129, 199, 227

Reference Example 2: Synthesis of Wittig reagent (2-methyl-2-propenyltriphenylphosphonium chloride) Triphenylphosphine (1000.0 g, 3.81 mol), 2-methyl-2-propenyl chloride (420) were added to a 5 L four-necked flask. 0.0 g, 4.64 mol, 1.2 eq.) And xylene (2390 g) were charged, and the mixture was heated to reflux for 19 hours. Thereafter, the reaction solution was cooled to room temperature, filtered through filter paper, washed with toluene (1000 g), and then dried with an evaporator and a vacuum pump to obtain 1001.7 g of 2-methyl-2-propenyltriphenylphosphonium chloride. (Yield 74.5%).

Example 2: Synthesis of morpholine amide compound (compound of formula (1)) In a 10 L four-necked flask, the Wittig reagent (988.0 g, 2.81 mol, 1.5 eq.) Synthesized in Reference Example 2 and tetrahydrofuran ( 1800 g, dehydrated with MS 5Å), stirred under a nitrogen atmosphere, sodium hydride (110.0 g, 2.75 mol, 1.5 eq.) Was quickly added thereto, and hydrogen generation was stopped until Stir at 50 ° C. for 2 hours. Thereafter, the reaction solution was cooled to 10 ° C., and a crude product of the aldehyde represented by the formula (6) (438.5 g, purity 95.1%, assuming 1.83 mmol) and tetrahydrofuran (200 g) were added. The mixture was dropped using a dropping funnel in 20 minutes, and after the dropping, the mixture was heated to reflux for 3 hours. The reaction solution was cooled to room temperature, quenched with methanol (20 g), added heptane (2000 g), and stirred for 30 minutes. It was filtered through Celite, and the filtrate was washed with 20% brine (2000 g) and 10% aqueous sodium carbonate solution (2000 g) in this order, then dried and concentrated to obtain 576.9 g of a crude product. Of these, 349.0 g was distilled and purified at 130 ° C. and 10 Pa to obtain 251.1 g of the morpholine amide compound represented by the formula (1) (2 stage yield: 70.6%).

  Further, as a result of gas chromatographic analysis of the morpholine amide compound represented by the formula (1) obtained in Example 2 above, the chemical purity was 85.4% (analysis conditions, column: TC-1701). (30 m × 0.53 mm), temperature rising conditions: 100 ° C. to 260 ° C., holding for 2 min at 100 ° C., 20.0 ° C./min temperature rising, carrier gas: nitrogen, linear velocity: 60 cm / sec, holding time: 11.3 min).

Physical property data of formula (1) morpholine amide compound
¹ H-NMR (400 MHz, CDCl ₃ ): δ ppm 0.85 (d, J = 6.8 Hz, 3H), 0.90 (d, J = 6.8 Hz, 3H), 1.50-1.67 ( m, 2H), 1
. 78-1.91 (m, 5H), 2.13-2.31 (m, 2H), 3.38-3.43 (m, 2H), 3.54-3.66 (m, 6H), 4.86-4.89 (m, 2H), 5.38 (dd, J = 9.2 Hz, 15.6 Hz, 1H), 6.07 (d, J = 15.6 Hz, 1H)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ ppm 18.8, 19.2, 20.7, 27.7, 31.2, 32.5, 41.8, 45.9, 49.5, 66. 6, 66.9, 114.6, 132.2, 134.4, 141.9, 171.9
MS (m / z): 57, 70, 86, 87, 88, 114, 129, 265

Example 3: Synthesis of solanone (compound of formula (8)) In a 1 L four-necked flask, a morpholine amide compound represented by formula (1) (90.00 g, assuming a purity of 85.4%, 290 mmol), Tetrahydrofuran (160 mL, dehydrated with MS5Å) was charged, and the mixture was stirred under cooling with ice water under a nitrogen atmosphere. A tetrahydrofuran solution of 2.0 M methylmagnesium chloride (174 mL, 348 mmol, 1.2 eq.) Was added to 5 to 15. Added at 30 ° C. over 30 minutes. After dropping, the mixture was stirred at the same temperature for 20 minutes, and then stirred at room temperature for 1 hour and 40 minutes. The reaction solution was added to a cooled flask containing 10% sulfuric acid (1200 g) at 5 ° C. or lower to adjust the pH to 1, followed by stirring for 15 minutes. Thereafter, the reaction solution was extracted with methyl t-butyl ether (600 mL), and the organic layer was washed with 20% brine (200 g) and 5% aqueous sodium carbonate solution (200 g) in that order, and then dried and concentrated to obtain a crude product. 77.40 g was obtained.

  This crude product was purified by distillation under reduced pressure to obtain 37.51 g of solanone represented by the formula (8) (yield 56.9%).

Formula (8) Physical property data of solanon
¹ H-NMR (400 MHz, CDCl ₃ ): δ ppm 0.84 (d, J = 6.8 Hz, 3H), 0.89 (d, J = 6.8 Hz, 3H), 1.42-1.67 ( m, 2H), 1.72-1.86 (m, 5H), 2.10 (s, 3H), 2.26-2.47 (m, 2H), 4.86-4.89 (m, 2H), 5.35 (dd, J = 9.2 Hz, 16.0 Hz, 1H), 6.06 (d, J = 16.0 Hz, 1H)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ ppm 18.7, 19.2, 20.7, 26.2, 30.1, 32.3, 42.1, 49.4, 114.6, 132. 2,134.4, 141.9, 209.3
MS (m / z): 41, 43, 79, 91, 93, 121, 136, 194
The major diastereomer was determined to be E form from the binding constant of ¹ H-NMR.

  In addition, as a result of gas chromatographic analysis of the solanone represented by the formula (8) obtained in Example 3 above, the chemical purity was 96.8% (total of E and Z isomers) (analysis conditions, Column: TC-1701 (30 m × 0.25 mm), temperature rising conditions: 70 ° C. to 220 ° C., 3 ° C./min temperature rising, carrier gas: nitrogen, linear velocity: 27 cm / sec, holding time: Z body 21.7 min , E body 22.2 min). Furthermore, the diastereomeric ratio was determined to be E: Z = 12: 1 by gas chromatographic analysis.

Claims (4)

A compound represented by the following formula (1).

It is a manufacturing method of the compound represented by Formula (1) of Claim 1, Comprising:
Following formula (4)

N- (3-methyl-1-butenyl) piperidine represented by the following formula (5)

And 4-acryloylmorpholine represented by the following formula (6):

Obtaining a compound represented by:
The compound represented by the formula (6) thus obtained was added to the following formula (7)

(Wherein X represents a halogen atom and Ph represents a phenyl group), which comprises a step of causing a Wittig reaction with a halogenated 2-methyl-2-propenyltriphenylphosphonium. Following formula (8)

A method for producing solanone represented by:
A production method comprising a step of reacting a Grignard reagent capable of converting a morpholinamide moiety of a compound represented by the formula (1) according to claim 1 into methylcarbonyl. A compound represented by the following formula (6).