JPH05112483A - Production of ether compound - Google Patents

Abstract

PURPOSE:To obtain in an industrially advantageous way an ether compound as an intermediate for synthesizing medicines, etc., by reaction of each specific two kinds of compounds in a non-aqueous solvent. CONSTITUTION:The objective compound of formula A-CH2CH2-O-B {e.g. 4-[2(5- ethyl-2-pyridyl)ethoxy]benzaldehyde} can be obtained by reaction between (A) a compound of formula A-CH2CH2-X [A is aromatic residue, R<1>-CO (R<1> is aliphatic hydrocarbon residue, aromatic hydrocarbon residue, etc.) or R<2>-CH=CH (R<2> is the same as R<1>); X is eliminable group] and (B) a compound of formula MO-B (M is alkali metal or alkaline earth metal; B is aromatic ring residue) in a non-aqueous solvent (e.g. methanol, acetone) pref. at 70-90 deg.C for 3-6hr. It is preferable that the amounts of the non-aqueous solvent and the component B to be used be 10-15 wt. times and 1.5-2 molar times the component A, respectively.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an industrially advantageous method for producing ethers which are synthetic intermediates for medicines and the like.

[0002]

2. Description of the Related Art As a compound having a phenol ether bond in the molecule, for example, a thiazolidinedione derivative having a blood glucose and blood lipid lowering action is known (JP-A-55-22636, JP-A-55-64586). According to these descriptions, 2-pyridyl ethanol is used as a starting material, and a phenol ether bond is formed by a substitution reaction of these with p-fluoronitrobenzene on a benzene ring, followed by reduction of a nitro group and meabaine acylation ( After the Meerwein acylation reaction, a thiazolidinedione derivative is produced by constructing a thiazolidine ring. However, p-fluoronitrobenzene used for the phenol ether bond-forming reaction is expensive and difficult to obtain industrially in large quantities, and the nitro group of the reaction product is converted into a carbon chain to form a thiazolidinedione ring. It requires a large number of steps for constructing, and cannot be said to be an industrially advantageous manufacturing method. On the other hand, as an industrially advantageous production method, after tosylation of 2-pyridylethanols, Williamson (Williamso) of this and p-hydroxybenzaldehyde is formed.
n) Phenol ether synthesis is carried out by the synthetic method,
A method for producing a 2,4-thiazolidinedione derivative is known (Japanese Patent Laid-Open No. 63-139182). This method has a smaller number of steps than the above-mentioned method for producing a thiazolidinedione derivative, and the desired thiazolidinedione derivative can be obtained in a relatively high yield.The Williamson synthetic method, which is one step of this route, is There are many by-products, and separation from the desired product is troublesome.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides an industrially advantageous method for producing ethers which can be synthetic intermediates for drugs and the like.

[0004]

The present invention provides a compound of the general formula A-CH ₂ CH ₂ -X (I) << wherein A is an aromatic ring residue, R ¹ -CO- (in the formula) , R ¹ is an aliphatic hydrocarbon residue, an aromatic hydrocarbon residue, a heterocyclic residue,
An araliphatic hydrocarbon residue or an alicyclic hydrocarbon residue is shown. Or R ² —CH═CH— (wherein R ² is an aliphatic hydrocarbon residue, an aromatic hydrocarbon residue, a heterocyclic residue, an araliphatic hydrocarbon residue or an alicyclic hydrocarbon residue). Indicates a group.)
X represents a leaving group. And a compound represented by the general formula MO-B (II) (wherein M represents an alkali metal atom or an alkaline earth metal atom, and B represents an aromatic ring residue). (wherein, a and B are the same as defined above.) general formula _{a-CH 2 CH 2 -O-} B which comprises reacting (III) is a method for producing ether compounds represented by.

In the above general formulas (I) and (III), examples of the aromatic ring residue represented by A include an aromatic hydrocarbon residue and an aromatic heterocyclic ring residue. Examples thereof include a phenyl group and a naphthyl group, and examples of the aromatic heterocyclic ring residue include a furyl group (2-furyl, 3 having 3 to 4 oxygen atoms, sulfur atoms and nitrogen atoms as ring-constituting atoms). -Furyl), thienyl group (2-thienyl, 3-thienyl), pyridyl group (2-pyridyl, 3-
Pyridyl, 4-pyridyl), thiazolyl (2-thiazolyl, 4-thiazolyl, 5-thiazolyl), triazolyl (1,2,4-triazol-1-yl, 1,2,3-triazol-1-yl, 1, 3,4-triazol-1-yl, 1,2,5-triazol-1-yl), tetrazolyl (1-tetrazolyl, 5-tetrazolyl) and the like. These groups cause β-elimination of the —O—B group in the formula (III) to facilitate the formation of a resonance stabilizing structure. These aromatic ring residues may have a substituent at any position on the ring, and the substituent may be any as long as it does not adversely affect the reaction, for example, methyl, Alkyl groups having 1 to 6 carbon atoms, such as ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, preferably carbon number 1-3
Such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t
An alkoxy group having 1 to 4 carbon atoms such as butoxy, preferably having 1 to 3 carbon atoms, for example, a halogen atom such as fluorine, chlorine and bromine, for example formyloxy, acetyloxy, propionyloxy, butyryloxy, isobutyryloxy, Alkanoyloxy groups having 6 or less carbon atoms such as pivaloyloxy and hexanoyloxy, arylcarbonyloxy groups such as benzoyloxy and 1-naphthoyloxy, and alkoxycarbonyl having 2 to 5 carbon atoms such as methoxycarbonyloxy and ethoxycarbonyloxy. An oxy group etc. are mentioned.

R ¹ --CO-- and R ² --CH represented by A
In CH = CH-, examples of the aliphatic hydrocarbon residue represented by R ¹ and R ² include methyl, ethyl, n-propyl, i-
Propyl, n-butyl, i-butyl, t-butyl, n-
C1-C6 alkyl groups such as pentyl, i-pentyl, neopentyl, n-hexyl, preferably C1
To alkenyl groups having 5 or less carbon atoms such as vinyl and allyl. Examples of the aromatic hydrocarbon residue represented by R ¹ and R ² include phenyl and naphthyl, and examples of the aromatic and aliphatic hydrocarbon residue include benzyl, phenethyl, naphthylmethyl, and naphthylethyl. As the heterocyclic ring residue, in addition to the aromatic heterocyclic ring residue in the aromatic ring residue represented by A, for example, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothienyl, dihydrothienyl, tetrahydropyranyl, dihydropyranyl , Piperidinyl, morpholinyl, pyrrolidinyl, piperazinyl, N-methylpiperazinyl and the like. These aromatic hydrocarbon residue, heterocyclic ring residue and araliphatic hydrocarbon residue may have a substituent at any position on the ring, and the substituent is an aromatic ring represented by A. The same as the substituent of the residue can be mentioned. R ¹ , R ²
Examples of the alicyclic hydrocarbon residue represented by are cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups and other cycloalkyl groups having 3 to 7 carbon atoms.

Examples of the leaving group represented by X in the above general formula (I) include halogen (chlorine, bromine, iodine, etc.), alkylsulfonyloxy group (methylsulfonyloxy, ethylsulfonyloxy, propylsulfonyloxy, etc.) 1 to 3), and arylsulfonyloxy (having 6 to 8 carbon atoms such as phenylsulfonyloxy, p-toluenesulfonyloxy, etc.), among which an arylsulfonyloxy group or an alkylsulfonyloxy group is preferable. The general formula (II)
In the above, examples of the alkali metal atom represented by M include potassium, sodium and lithium, and examples of the alkaline earth metal atom include magnesium, calcium and
Examples include strontium and barium. In the general formulas (II) and (III), the aromatic ring residue represented by B is the same as the aromatic ring residue represented by A. Examples of these substituents include aldehyde and the like in addition to the substituent of the aromatic ring residue represented by A.

In the method of the present invention, the reaction between compound (I) and compound (II) is carried out in a non-aqueous solvent. The non-aqueous solvent is an organic solvent that does not substantially contain water, more specifically, an organic solvent having a water content of 5% or less, preferably 3% or less. Examples thereof include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, and t-butanol, ketones such as acetone, methyl ethyl ketone, diethyl ketone, and methyl isobutyl ketone, ethers such as dioxane and tetrahydrofuran, dichloroethane. , Aliphatic halogenated hydrocarbons such as chloroform, acetonitrile, N, N-dimethylformamide, dimethyl sulfoxide, hexamethylsulphophosphorus triamide, and the like. These can be used alone or as a mixed solvent, but are particularly alcohols. , Ketones,
Hydrophilic compounds such as ethers, acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphorus triamide are preferable. The amount of solvent used is 5 to 30 times by weight, preferably 10 to 15 times by weight, relative to compound (I). The non-aqueous solvent preferably has a low water content, but if it is 5% or less, there is substantially no problem. When the non-aqueous solvent contains a large amount of water, the hydrate formation and dissociation of the compound (II) deteriorates the yield, which is not preferable. The amount of the compound (II) used is usually in an excess molar amount with respect to the compound (I), preferably 1.5 to 2 mol. The reaction temperature can be from room temperature to the reflux temperature of the solvent, but since compound (I) is apt to cause a β-elimination reaction due to its structure, it is 50 because of the relationship between the β-elimination reaction and the reaction time.
-120 degreeC is preferable and 70-90 degreeC is more preferable. The reaction time varies depending on the reaction conditions such as the reaction temperature, but is usually 1 when the reaction temperature is 50 to 120 ° C.
~ 15 hours, in the case of 70 ~ 90 ℃ usually 3 ~ 6 hours.

The target compound of this reaction is obtained by subjecting the reaction solution to known separation and purification means to obtain the target compound (III).
Can be isolated and purified, but the desired product (II
Since the content of I) is high, it can be used as it is in the reaction of the next step. (In the formula, A are the same as defined above.) The compound represented by formula (I), for example the general formula _{A-CH 2 CH 2 -OH (} IV) a halogenating agent to the compound represented by or It can be produced by reacting a sulfonyl halide. Examples of the halogenating agent include thionyl chloride, phosphorus oxychloride, phosphorus tribromide, and the like, and examples of the sulfonyl halide include methanesulfonyl chloride, ethanesulfonyl chloride, propanesulfonyl bromide, and the like.
4 alkanesulfonyl halides such as benzenesulfonyl chloride, p-toluenesulfonyl chloride, p-toluenesulfonyl bromide and the like having 6 carbon atoms
-8 arene sulfonyl halides. Of these, alkane- and arene-sulfonyl halides are preferable. The amount of the halogenating agent or the sulfonyl halide used is 1 to 3 times mol, preferably 1 to 1.2 times mol, of the compound (IV).

This reaction is usually carried out in a solvent in the presence of a base. Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloroethane and chloroform, ethers such as tetrahydrofuran and dioxane, and ketones such as acetone and methylethylketone. , Acetonitrile, N,
Examples thereof include N-dimethylformamide or a mixed solvent of these with water, and examples of the base include tertiary amines such as triethylamine, tripropylamine, tributylamine, and pyridine, such as sodium hydroxide,
Examples thereof include alkali metal hydroxides such as potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, as well as sodium hydride and sodium acetate. The amount of the base used is 1 to 3 times, preferably 1 to 1.2 times the mol of the compound (IV). This reaction is usually carried out at 0 to 40 ° C, preferably 0 to 25 ° C. The reaction time is usually 0.5 to 5 hours.

The reaction of the present invention can be used for the synthesis of various compounds, one example of which is shown. In the general formula (I),
When a compound in which A is a 5-ethyl-2-pyridyl group and a compound in which B in the general formula (II) is a phenyl group having a formyl group at the p-position are reacted by the method of the present invention, 4-
[2- (5-Ethyl-2-pyridyl) ethoxy] benzaldehyde is obtained. This and 2,4-thiazolidinedione were added to Knoevenagel gel (Kno
The reaction of 5- [4-
[2- (5-Ethyl-2-pyridyl) ethoxy] benzylidene] -2,4-thiazolidinedione is obtained, and by further reducing it, it has a blood glucose and blood lipid lowering action and is used as a drug such as a therapeutic agent for diabetes. Used 5-
[4- [2- (5-ethyl-2-pyridyl) ethoxy]
Benzyl] -2,4-thiazolidinedione. When applying the method of the present invention to this series of steps,
The target compound obtained by the method of the present invention is disclosed in JP-A-63-63
-1392- because there are no impurities that are difficult to separate as compared with the one obtained by the method described in 139182, 4- [2- (5-ethyl-2-pyridyl) ethoxy]
Even when the reaction mixture containing benzaldehyde was directly used in the next condensation reaction with 2,4-thiazolidinedione, 5- [4- [2- (5-ethyl-2-pyridyl) ethoxy] benzylidene] -2,4 -Thiazolidinedione can be obtained in a higher yield, and even when used in the next reduction step without further purification, 5- [4- [2-
(5-Ethyl-2-pyridyl) ethoxy] benzyl]-
2,4-thiazolidinedione can be obtained in high yield.

[0012]

EFFECTS OF THE INVENTION According to the present invention, it is possible to produce high-quality phenol ethers with a short reaction time and a high yield as compared with the known method, and to obtain good results in yield and quality in the next step. Bring In addition, the production method of the present invention is highly safe and has good operability, and is industrially extremely advantageous.

[0013]

【Example】

(Reference Example 1) Production of potassium 4-formylphenolate 81.3 g of potassium hydroxide (85% content) was dissolved in 1.08 liter of ethanol with stirring, and 150 g of p-hydroxybenzaldehyde was dissolved therein at room temperature.
Stir for hours. The reaction mixture was concentrated under reduced pressure, 350 ml of ethanol was added to the residue, and the mixture was concentrated again. To the residual solid content, 200 ml of ethanol was added, 2.1 l of diisopropyl ether was further added, and the mixture was stirred at room temperature for 1 hour. The obtained precipitate was filtered under reduced pressure and washed with 150 ml of diisopropyl ether. It was dried under reduced pressure at 40 ° C. to obtain 197 g (yield 100%) of potassium 4-formylphenolate.

Reference Example 2 Preparation of (5-ethyl-2-pyridyl) ethyl methanesulfonate 80 g of (5-ethyl-2-pyridyl) ethanol was dissolved in 800 ml of methylene chloride, and 55 g of triethylamine was added. 73.2 g of methanesulfonyl chloride was gradually added dropwise to this mixture with cooling and stirring, and the mixture was stirred at room temperature for 3 hours. 400 ml of water was added to the reaction solution for liquid separation, and the aqueous layer was back-extracted with 130 ml of methylene chloride to combine the extracted organic layers. The organic layer was washed with 400 ml of saturated aqueous sodium hydrogen carbonate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give (5-ethyl-2-pyridyl) ethyl methanesulfonate 12
1 g (100%) was obtained as a pale yellow oil. IR (Neat) ν cm ^-1 : 1360, 1200, 11
80 NMR (CDCl ₃ ) δppm: 1.23 (3H, t,
J = 7.5 Hz), 2.65 (2H, q, J = 7.5H)
z), 2.88 (3H, s), 3.20 (2H, t, J
= 6.5 Hz), 4.62 (2H, t, J = 6.5H)
z), 7.17 (1H, d, J = 7.5 Hz), 7.5
2 (1H, dd, J = 7.5Hz, 3.0Hz), 8.
38 (1H, d, J = 3.0Hz)

(Reference Example 3) Preparation of (5-ethyl-2-pyridyl) ethyl p-toluenesulfonate 7.1 g of sodium hydroxide was added to 33 ml of water, and 7.6 g of (5-ethyl-2-pyridyl) ethanol was added. Was dissolved in 33 ml of tetrahydrofuran, and both were mixed and cooled. A solution prepared by dissolving 11.7 g of p-toluenesulfonyl chloride in 51 ml of tetrahydrofuran was slowly added dropwise to the cooled stirring solution at 0 ° C., and the mixture was stirred at the same temperature for 2 hours after the dropping. Ice water was added to the reaction mixture, and the mixture was extracted twice with 100 ml of methylene chloride. The extracted organic layers were combined, washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 14.4 g (yield 94.4%) of (5-ethyl-2-pyridyl) ethyl p-toluenesulfonate as a pale yellow oily substance. IR (Neat) ν cm ^-1 : 1360, 1190, 11
80 NMR (CDCl ₃ ) δppm: 1.22 (3H, t,
J = 7.5 Hz), 2.41 (3H, s), 2.60
(2H, q, J = 7.5 Hz), 3.08 (2H, t,
J = 6.8 Hz), 4.41 (2H, t, J = 6.8H)
z), 7.03 (1H, d, J = 7.6 Hz), 7.2
6 (2H, d, J = 7.5Hz) 7.41 (1H, dd, J = 7.6Hz, 3.0H
z), 7.68 (2H, d, J = 7.5 Hz), 8.2
5 (1H, d, J = 3.0Hz)

(Example 1) b) Preparation of 4- [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde (5-ethyl-2-pyridyl) ethyl methanesulfonate 72 g and potassium 4-formylphenolate 8
5.5 g of ethanol was dissolved in 850 ml of ethanol and stirred under reflux for 6.5 hours. The reaction mixture was concentrated under reduced pressure, 850 ml of ethyl acetate was added to the residue, and the mixture was washed 5 times with 700 ml of 0.2N aqueous sodium hydroxide solution and twice with 700 ml of water, and dried over anhydrous sodium sulfate. After treating the organic layer with 7.0 g of activated carbon, the solvent was distilled off under reduced pressure.
67 g of an oil containing [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde was obtained. This product is purified by subjecting it to silica gel column chromatography, and then 4- [2
56.0 g of-(5-ethyl-2-pyridyl) ethoxy] benzaldehyde was obtained as a pale yellow oil, and the yield from [(5-ethyl-2-pyridyl) ethyl methanesulfonate was 70.0%. ]. This product is a standard product and IR
(Neat) and NMR (CDCl ₃ ) were in perfect agreement. IR (Neat) νcm ^-1 : 1695, 1605, 15
80, 1260, 1160 NMR (CDCl ₃ ) δppm: 1.23 (3H, d,
J = 7.5 Hz), 2.63 (2H, q, J = 7.5H)
z), 3.25 (2H, t, J = 6.5Hz), 4.4
4 (2H, t, J = 6.5Hz), 6.98 (2H,
d, J = 8.5 Hz), 7.17 (1H, d, J = 7.
5Hz), 7.46 (1H, dd, J = 7.5Hz,
3.0 Hz) 7.78 (2H, d, J = 8.5 Hz),
8.39 (1H, d, J = 3.0Hz), 9.83 (1
H, s)

B) Preparation of 4- [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde 151 g (5-ethyl-2-pyridyl) ethyl methanesulfonate (content 94%) and 179 g potassium 4-formylphenolate Was dissolved in 1.5 liters of ethanol, and the mixture was stirred under reflux for 5 hours. The reaction solution was concentrated under reduced pressure, and 1.7 L of ethyl acetate was added to the residue to give 0.2N.
It was washed with 500 ml of an aqueous solution of caustic soda three times, then with 500 ml of water, and dried with anhydrous sodium sulfate. The organic layer was treated with 6.3 g of activated carbon, and the solvent was distilled off under reduced pressure.
141.5 g of an oil containing-[2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde was obtained. This product was quantified by HPLC and confirmed to contain 119 g of 4- [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde. The yield from [(5-ethyl-2-pyridyl) ethyl methanesulfonate was It was 75.3%. ].

C) Preparation of 4- [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde 14 g of (5-ethyl-2-pyridyl) ethyl p-toluenesulfonate and 14.7 g of potassium 4-formylphenolate are prepared. It was dissolved in 200 ml of ethanol and stirred under reflux for 5 hours. The reaction solution was concentrated under reduced pressure, 200 ml of ethyl acetate was added to the residue, and 100 ml of 0.2N aqueous sodium hydroxide solution was added 5 times, followed by 1 part of water.
It was washed twice with 50 ml and dried over anhydrous sodium sulfate.
The organic layer was treated with 1 g of activated carbon, and the solvent was distilled off under reduced pressure.
10.5 g of a red oil containing [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde was obtained. This product was quantified by HPLC, and it was confirmed that 8.2 g of 4- [2- (5-ethyl-2-pyridyl) ethoxy] benzaldehyde was contained. The yield from [(5-ethyl-2-pyridyl) ethyl methanesulfonate was 70.1%. ].

Reference Example 4 Preparation of 5- [4- [2- (5-ethyl-2-pyridyl) ethoxy] benzylidene] -2,4-thiazolidinedione Treated in the same manner as in Example 1B). Obtained 4- [2-
94 g of (5-ethyl-2-pyridyl) ethoxy] benzaldehyde (content 80.6%) was dissolved in 1.1 liter of ethanol, and 93.7 g of 2,4-thiazolidinedione was dissolved.
And 19.7 g of piperidine were added, and the mixture was stirred under reflux for 5 hours. The reaction solution was gradually cooled to room temperature, and the resulting crystals were filtered under reduced pressure. The crystals were washed with 100 ml of ethanol and dried at 50 ° C. under reduced pressure to give 5- [4-
Light yellow crystals of [2- (5-ethyl-2-pyridyl) ethoxy] benzylidene] -2,4-thiazolidinedione 7
7.1 g (content 99.5%) was obtained (4- [2- (5-
The yield from ethyl-2-pyridyl) ethoxy] benzaldehyde was 73.0%. ). This product is the standard 5-
[4- [2- (5-ethyl-2-pyridyl) ethoxy]
Benzylidene] -2,4-thiazolidinedione and various spectral data were in perfect agreement.

Reference Example 5 Preparation of 5- [4- [2- (5-ethyl-2-pyridyl) ethoxy] benzyl] -2,4-thiazolidinedione Obtained by treating in the same manner as in Reference Example 4. 5- [4- [2-
30 g of (5-ethyl-2-pyridyl) ethoxy] benzylidene] -2,4-thiazolidinedione is suspended in 600 ml of dioxane, 20 g of 5% palladium-carbon (50% wet) is added, and hydrogen is applied at 110 ° C. It was catalytically reduced under (100 kg / cm ² ) for 2 hours. The catalyst was filtered off while hot, and the filtrate was concentrated under reduced pressure to about 540 ml. Precipitated crystals were collected by filtration, and the obtained crystals were dissolved in 600 ml of dioxane while hot, and slowly cooled to room temperature for recrystallization. The obtained crystals were collected by filtration under reduced pressure to give 6
After drying under reduced pressure at 0 ° C, 5- [4- [2- (5-ethyl-2
21.7 g of (-pyridyl) ethoxy] benzyl] -2,4-thiazolidinedione were obtained (5- [4- [2- (5-
Ethyl-2-pyridyl) ethoxy] benzylidene]-
The yield from 2,4-thiazolidinedione was 72%. ). The spectrum data of this product completely matched the authentic data of 5- [4- [2- (5-ethyl-2-pyridyl) ethoxy] benzyl] -2,4-thiazolidinedione.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI technical display location C07D 249/04 249/08 257/04 7019-4C 277/24 7019-4C 307/40 333/16

Claims (1)

[Claims] 1. In a non-aqueous solvent, a compound represented by the general formula A-CH ₂ CH ₂ -X << wherein A is an aromatic ring residue, R ¹ --CO-- (wherein R ¹ is an aliphatic hydrocarbon residue, Aromatic hydrocarbon residue, heterocyclic ring residue,
An araliphatic hydrocarbon residue or an alicyclic hydrocarbon residue is shown. Or R ² —CH═CH— (wherein R ² is an aliphatic hydrocarbon residue, an aromatic hydrocarbon residue, a heterocyclic residue, an araliphatic hydrocarbon residue or an alicyclic hydrocarbon residue). Indicates a group.)
X represents a leaving group. A compound represented by general formula MO-B (in the formula, M represents an alkali metal atom or an alkaline earth metal atom, and B represents an aromatic ring residue). preparation of an ether compound represented by the general formula _{a-CH 2 CH 2 -O-} B , wherein (wherein, a and B are as defined above.).