JP2001261673A - Cyano compound and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method of simply and efficiently producing a cyanoacetoacetic acid derivative and an intermediate that is used in this production process. SOLUTION: 6-(Halogenated methyl)-4H-2, 3-dioxin-4-one is allowed to react with a cyanidation agent to produce 6-cyanomethyl-4H-2,3-dioxin-4-one, then the resultant 6-cyanomethyl-4H-2,3-dioxin-4-one is allowed to react with an alcohol or water to produce a cyanoacetoacetic derivative according to the following formula, wherein X is a halogen atom, R1 and R2 are identical or different from each other and represent each a leaving group together with the oxygen atom adjacent to the carbonyl group; R3 is H or a hydrocarbon group which may be substituted).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an intermediate useful for obtaining a cyanoacetoacetic acid derivative useful as a fine chemical intermediate for pharmaceuticals, agricultural chemicals and the like, a method for producing the same, and the production of a cyanoacetoacetic acid derivative using the intermediate. About the method.

[0002]

2. Description of the Related Art Cyanoacetoacetic acid derivatives are compounds useful as fine chemical intermediates for pharmaceuticals, agricultural chemicals and the like.

[0003] As a method for synthesizing this compound, for example, Journal of Chemical Society Chemical Communica
tion, Vol. 24, pp. 932-933 (1977), in the presence of sodium hydride, at −30 ° C., the raw material 4-bromoacetoacetate is stirred to be chelated, and further reacted with N≡C ^−. A method for synthesizing ethyl cyanoacetoacetate is described. However, in this method, in addition to the low handling property of sodium hydride, chelation of the raw material is performed at -30 ° C.
And low temperature, the reaction operability decreases, which is disadvantageous in industrial practice.

As a method for producing acetoacetates, for example, Chemistry letters, vol. 6, pages 901-904 (19)
90) has 6- (α-hydroxyethyl) -4H-1,
Opening the 3-dioxin-4-one with methanol,
A method for synthesizing methyl 1-hydroxyethylcarbonylacetate is described. Also, Journal of OrganicChem
In Istry, Vol. 62, No. 21, p. 7114 (1997), alcohol or water is allowed to act on acetylketene derived from 6-methyl-4H-1,3-dioxin-4-one. Acetate is synthesized. However, these documents include 6-cyanomethyl-4
There is no description of the H-1,3-dioxin-4-one derivative, and these reaction systems are described as 6-cyanomethyl-4H-.
There is no example applied to 1,3-dioxin-4-one derivatives.

[0005]

Accordingly, an object of the present invention is to provide a cyano compound useful for efficiently producing an acetoacetic acid derivative, a method for producing the same, and a method for producing an acetoacetic acid derivative using the cyano compound. Is to provide.

[0006]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a cyanoacetoacetic acid derivative can be efficiently produced by using a specific cyano compound, thereby completing the present invention. .

That is, the cyano compound of the present invention is represented by the following formula (1).

[0008]

Embedded image

(Wherein, R ¹ and R ² are the same or different and each represent a group capable of leaving together with an oxygen atom adjacent to a carbonyl group. R ¹ and R ² form a ring together with an adjacent carbon atom) In the above formula (1), R ¹ and R ² are the same or different and are an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, a heterocyclic group or the like, and R ¹ and R ² are May form a cycloalkane ring, a heterocyclic ring or the like with adjacent carbon atoms.

The cyano compound (1) is represented by the following formula (2)

[0011]

Embedded image

Wherein X is a halogen atom; R ¹ and R ² are the same as defined above;
It can be produced by reacting with a cyanating agent. The reaction may be performed in the presence of an amine salt, an ammonium salt, an alkali metal halide, a cyclic polyether, or the like, if necessary.

In the present invention, the cyano compound (1) is
By reacting with an alcohol or water represented by the following formula (3), a cyanoacetoacetic acid derivative represented by the following formula (4) is produced.

[0014]

Embedded image

(Wherein R ³ represents a hydrogen atom or a hydrocarbon group which may have a substituent)

[0016]

BEST MODE FOR CARRYING OUT THE INVENTION [Cyano compound (1)] In the cyano compound represented by the above formula (1), R ¹ and R
² is not particularly limited as long as it can be eliminated together with the oxygen atom adjacent to the carbonyl group (that is, the oxygen atom at the 3-position of the dioxin ring) upon opening of the dioxin ring. The elimination is performed by the σ bond between the oxygen atom at position ¹ and the carbon atom at position 2 (the carbon atom to which R ¹ and R ² are bonded) of the dioxin ring, and the oxygen atom at position 3 and the carbonyl at position 4 Σ with carbon
It occurs when the bond is broken and the ring opens.

As such R ¹ and R ² , groups which do not participate in the ring-opening reaction of the cyano compound (1) to the cyanoacetoacetic acid derivative (4), for example, an aliphatic hydrocarbon group and an alicyclic hydrocarbon group , An aromatic hydrocarbon group, a heterocyclic group and the like. These plural groups may be bonded.

The aliphatic hydrocarbon group may be linear or branched, and may be saturated or unsaturated. Examples of such an aliphatic hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group and t-butyl group (preferably C _1-10 alkyl group, more preferably C _1-
6 alkyl groups, especially C _1-4 alkyl groups, etc.); vinyl groups,
An alkenyl group such as an allyl group, an isopropenyl group, a 1-butenyl group and a 2-butenyl group (preferably a C _2-6 alkenyl group, particularly a C _2-4 alkenyl group); an ethynyl group,
An alkynyl group such as a propynyl group, a 1-butynyl group and a 2-butynyl group (preferably a C _2-6 alkynyl group;
_2-4 alkynyl group).

The alicyclic hydrocarbon group may be saturated or unsaturated. For example, a cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cyclooctyl group (for example,
_A cycloalkenyl group such as a _3-10 cycloalkyl group, preferably a C _4-8 cycloalkyl group, particularly a C _4-6 cycloalkyl group; a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cyclooctenyl group ( For example, C _3-10 cycloalkenyl group, preferably C _4-8 cycloalkenyl group, especially C _4-6 cycloalkenyl group); cycloalkynyl group such as cyclopentynyl group, cyclohexynyl group, cyclooctynyl group (for example,
A C _4-8 cycloalkynyl group, particularly a C _5-6 cycloalkynyl group).

The aromatic hydrocarbon group includes an aryl group such as a phenyl group and a naphthyl group (C _6-10 aryl group); and an aralkyl group such as a benzyl group and a phenyl group (C _6-10 aryl-C _1-4). Alkyl group, etc.); C _6-10 aryl-C _2-4
An alkenyl group; and a C _6-10 aryl-C _2-4 alkynyl group.

The heterocyclic group includes a heterocyclic ring having at least one heteroatom selected from a nitrogen atom, an oxygen atom and a sulfur atom as a constituent atom of the ring (particularly, a 5- or 6-membered heterocyclic ring). The heterocyclic group may be non-aromatic or aromatic. Examples of the non-aromatic heterocyclic group include 5- to 10-membered heterocyclic groups such as pyrrolidinyl, piperidyl, piperidino, morpholinyl, and morpholino. As the aromatic heterocyclic ring corresponding to the aromatic heterocyclic group, pyrrole, pyridine, pyrazine,
Heterocycles containing a nitrogen atom such as pyrimidine and pyridazine; Heterocycles containing an oxygen atom such as furan; Heterocycles containing a sulfur atom such as thiophene; Nitrogen and heterocycles containing an oxygen atom such as oxazole and furazane; Nitrogen such as thiazole, thiadiazole and thiazine And a sulfur atom-containing heterocycle. Further, a heterocyclic group such as a furfuryl group -C
_1-4 alkyl groups and the like are also included.

The hydrocarbon group may have a substituent.
No. Such substituents include a fluorine atom, a chlorine atom
Halogen atom such as bromine atom and bromine atom; methyl group and ethyl group
Such as C_1-4Alkyl group; acyl group [such as acetyl group
Alkylcarbonyl group (C_1-4Alkyl-carbonyl group
Arylcarbonyl groups such as benzoyl group (C
_{6- Ten}Aryl-carbonyl group, etc.)]; acyloxy group
[Alkylcarbonyloxy group such as acetyloxy group
(C_1-4Benzoylo)
Arylcarbonyloxy groups such as xy group (C_6-10Ants
Methoxyl group, d)
An alkoxyl group such as a toxyl group (C_1-4Alkoxyl
Alkoxycarbonyl such as methoxycarbonyl group)
Bonyl group (C _1-4Alkoxy-carbonyl group etc.);
Aryl groups such as phenyl and naphthyl groups (C_6-10Ally
An aryloxy group such as a phenoxyl group;
Examples of the above-described heterocyclic groups can be given.

As the ring formed by R ¹ and R ² together with adjacent carbon atoms, an alicyclic hydrocarbon ring [C _3-10 cycloalkane (particularly C _{3 - 6} cycloalkane), C _3-10 cycloalkene (especially C _4-6 cycloalkene), etc.], an aromatic hydrocarbon ring (benzene corresponding to the aromatic hydrocarbon group exemplified above),
Heterocycle (5 to 10 membered heterocycle) and the like.

Preferred R ¹ and R ² are an alkyl group, a cycloalkyl group (especially a C _5-6 cycloalkyl group), an aryl group (especially a phenyl group), an aralkyl group (especially a benzyl group, a phenethyl group and the like), and And an aromatic heterocyclic group (5- or 6-membered aromatic heterocyclic group). Desirable R ¹ and R ² together with adjacent carbon atoms form a cycloalkane ring (particularly a C _3-6 cycloalkane ring) or a heterocyclic ring (a 5- to 10-membered heterocyclic ring, particularly a 5- to 8-membered heterocyclic ring). . Particularly preferred R ¹ and R ² are the same or different and are a C _1-4 alkyl group, especially a C _1-2 alkyl group.

Typical cyano compounds (1) include, for example, 6-cyanomethyl-2,2-dimethyl-4H-
1,3-dioxin-4-one, 6-cyanomethyl-
6-cyanomethyl-2,2-diC _1-6 alkyl-4H-1,3-dioxin-4-one such as 2,2-diethyl-4H-1,3-dioxin-4-one.

[Production method of cyano compound (1)] The cyano compound (1) can be produced by reacting the halogen compound represented by the formula (2) with a cyanating agent.

In the halogen compound (2), examples of X include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. X is usually a chlorine, bromine or iodine atom.

The cyanating agent is not particularly limited as long as it is a compound capable of generating cyan ions in the reaction system. Examples thereof include hydrogen cyanide and metal cyanides (eg, alkali metal cyanides such as sodium cyanide and potassium cyanide; cyanide). Alkaline earth metal cyanides such as calcium cyanide; transition metal cyanides such as copper cyanide), and organic cyanides (tri-C such as trimethylsilyl cyanide).
_1-4 alkylsilyl-cyanide, etc.). Preferred cyanating agents include hydrogen cyanide and metal cyanides.

The proportion of the cyanating agent can be selected from a wide range of about 0.1 to 100,000 mol per mol of the halogen compound (2), and is usually 0.5 to 1,000 mol (for example, 0 to 100 mol). 0.8 to 100 mol), preferably 1 to 5
It is about 0 mol (particularly 1 to 10 mol).

The cyanidation reaction of the halogen compound (2)
The reaction may be performed in the presence of a reaction aid. Examples of such a reaction aid include amine salts (tri-C ₁ -alkylamine hydrohalides such as trimethylamine hydrochloride, triethylamine hydrochloride and triethylamine bromate; heterocyclic tertiary such as pyridine hydrochloride). Amine hydrohalides; N, N-diC _1-4 alkylaniline hydrohalides such as N, N-dimethylaniline hydrochloride);
Ammonium salts (ammonium halides such as ammonium chloride, ammonium bromide and ammonium iodide;
Ammonium sulfate; ammonium nitrate; ammonium carbonate; ammonium phosphate, etc.), alkali metal halides [alkali metal bromide (sodium bromide, potassium bromide, etc.), alkali metal iodides (sodium iodide, potassium iodide, etc.)], and Cyclic polyethers (12-crown-4, 15-crown-5, 18-
Phase transfer catalysts such as crown ethers such as crown-6). These reaction aids can be used alone or in combination of two or more. Preferred reaction auxiliaries are ammonium salts, especially ammonium halides.

The amount of the reaction aid is not particularly limited, and is selected from a wide range of about 0.001 to 1000 moles per mole of the halogen compound (2), depending on the kind of the reaction aid. And preferably about 0.01 to 100 mol, more preferably about 0.1 to 10 mol (particularly 1 to 5 mol).

The reaction may be carried out in the presence or absence of a solvent. The solvent is not particularly limited as long as it does not inhibit the progress of the reaction and dissolves the reaction components. Water and organic solvents such as alcohols (methanol, ethanol, cyclohexanol, etc.), esters (acetic acid) Ethyl, etc.), ketones (acetone, methyl ethyl ketone, etc.), ethers (1,4-dioxane, tetrahydrofuran, diethyl ether, etc.), nitriles (acetonitrile, benzonitrile, etc.), sulfoxides (dimethylsulfoxide, etc.), sulfones ( Sulfolane), amides (dimethylformamide, etc.), aliphatic hydrocarbons (pentane, hexane, octane, etc.), alicyclic hydrocarbons (cyclohexane, etc.),
Aromatic hydrocarbons (benzene, toluene, etc.) and halogen-containing compounds (methylene chloride, chloroform, bromoform, chlorobenzene, halogenated hydrocarbons such as bromobenzene, etc.) can be used. These solvents can be used alone or in combination of two or more. The amount of the solvent is not particularly limited as long as the reaction components (such as the halogen compound (2)) can be dissolved.

The reaction is usually carried out at normal pressure. If necessary, the reaction may be carried out under reduced pressure or increased pressure in terms of the apparatus or operation.

The reaction temperature is not particularly limited as long as it is not lower than the melting point of the system and not higher than the boiling point under the reaction conditions.
The reaction temperature is 0 ° C to 300 ° C, preferably about -10 ° C to 200 ° C, and the reaction proceeds efficiently even under mild conditions at room temperature (5 to 40 ° C).

[Production Method of Cyanoacetoacetic Acid Derivative] In the present invention, the cyano compound (1) is reacted with the alcohol or water represented by the formula (3) to obtain
A cyanoacetoacetic acid derivative (cyanoacetoacetic acid or cyanoacetoacetate) represented by the above formula (4) is produced.

In this reaction, the method for synthesizing the cyano compound (1) is not particularly limited. For example, the cyano compound (1) may be produced by the method for producing the cyano compound (1) or may be produced by another method.

In the formulas (3) and (4), the hydrocarbon group represented by R ³ is an aliphatic hydrocarbon group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group exemplified in the section of R ¹ and R ^2. Group hydrocarbon groups and the like. Preferred R ³ is a hydrogen atom,
C _1-10 aliphatic hydrocarbon group (C _{1 -6} alkyl group, C _2-6 alkenyl, C _2-6 alkynyl group), C _3-10 alicyclic hydrocarbon group (C _4-8 cycloalkyl Group, C _4-8 cycloalkenyl group, C _4-8 cycloalkynyl group, etc., aryl group (C _6-10 aryl group such as phenyl group), aralkyl group (C _6-10 aryl such as benzyl group, phenethyl group, etc.) -C
_1-4 alkyl groups) and the like. Among them, a C _1-4 alkyl group such as a methyl group and an ethyl group is preferable.

Examples of the substituent which the group R ³ may have include the substituents exemplified in the above-mentioned R ¹ and R ² .

In the reaction for producing the cyanoacetoacetic acid derivative (4), the proportion of the alcohol or water (3) can be selected according to the starting material, reaction mode, reaction rate, etc., and is 0 to 1 mol of the cyano compound (1). 0.1 to 100,000 moles,
Preferably it is about 0.5 to 1,000 mol, more preferably about 0.8 to 100 mol.

The reaction for producing the cyanoacetoacetate derivative (4) can proceed by heating or the like even in the absence of a catalyst. However, the reaction may be promoted by the reaction in the presence of a catalyst. Such catalysts include various acid catalysts, for example, inorganic acids such as sulfuric acid, hydrochloric acid, phosphoric acid, and nitric acid;
Carboxylic acids (such as C _1-10 saturated or unsaturated mono- or polycarboxylic acids such as acetic acid and propionic acid), sulfonic acids (C _1-6 alkanesulfonic acids such as methanesulfonic acid and ethanesulfonic acid; benzenesulfonic acid, p Organic acids such as aromatic sulfonic acids such as toluenesulfonic acid), halogenated organic acids (halogenated carboxylic acids such as trifluoroacetic acid; halogenated alkanesulfonic acids such as trifluoromethanesulfonic acid); sulfates (sulfuric acid) Calcium, etc., metal oxides (SiO ₂ , Al ₂ O _3, etc.), zeolites (Y-type, X-type, A-type zeolites having acidic OH, etc.), ion exchange resins (cation exchange resins, such as H-type, etc.) Solid acids such as can be used. These catalysts can be used alone or in combination of two or more.

The amount of the catalyst to be used is not particularly limited, and is, for example, 0.001 to 1 mol, preferably 0.01 to 0.5 mol, and more preferably 0.01 to 1 mol, per 1 mol of the cyano compound (1). About 0.2 mol.

The reaction may be performed in the presence or absence of a solvent. As the solvent, for example, the same solvents (ketones, ethers, nitriles, sulfoxides, sulfones, amides, hydrocarbons, halogen-containing compounds, and the like) as those exemplified in the method for producing the cyano compound (1) are used. ) Can be used alone or in combination of two or more. Further, the alcohol or water (3) may be used as a solvent. When a C _1-6 alkyl alcohol such as methanol, ethanol or t-butanol is used as the alcohol (3), it is preferable to use the alcohol (3) as a solvent.

The reaction can be usually carried out at normal pressure, but may be carried out under reduced pressure or under increased pressure depending on the reaction conditions, reaction apparatus, operability and the like.

The reaction temperature may be generally from the melting point of the system to the boiling point under the reaction conditions.
The temperature is 300C, preferably -10C to 200C, and more preferably about 30 to 150C.

The production of the cyano compound (1) and the cyanoacetoacetic acid derivative (4) can be usually performed in air. If necessary, it may be performed in an atmosphere of an inert gas such as a nitrogen gas or an argon gas.

The production of the cyano compound (1) and the cyanoacetoacetic acid derivative (4) can be carried out by a conventional method such as a batch system, a semi-batch system and a continuous system.

When the cyano compound (1) is produced by the method of the present invention, and then the cyanoacetoacetic acid derivative (4) is produced, the cyano compound (1) is isolated and subjected to the step of producing the cyanoacetoacetic acid derivative (4). And may be subjected to the step of producing derivative (4) without separation and purification.

The cyano compound (1) and the cyanoacetoacetic acid derivative (4) were filtered, concentrated, distilled, extracted,
Ion exchange, electrodialysis, crystallization, recrystallization, adsorption, membrane separation,
It can be easily separated and purified by conventional separation and purification means such as centrifugation and chromatography (such as column chromatography) and combinations thereof.

The cyanoacetoacetic acid derivative obtained by such a method is useful as an intermediate in fine chemicals such as medicines and agricultural chemicals and as a raw material for polyamide.

[0050]

According to the present invention, a cyanoacetoacetic acid derivative can be industrially and advantageously produced efficiently using a novel compound, 6-cyanomethyl-4H-1,3-dioxin-4-one.

[0051]

The present invention will be described below in more detail with reference to Examples, but the present invention is not limited to these Examples.

In the examples, the IR spectrum was obtained from PERKIN-ELMER 1600 Series
s Measured using FT-IR.

The NMR spectrum was measured by BRUKER AM
500, 500 MHz ( ¹ H-NMR) or 12 MHz
At 5.7 MHz (< ¹³ > C-NMR), measurement was performed using tetramethylsilane (TMS) as an internal standard.

The MS spectrum was obtained from JEOL Ltd.
Using MS-SX102A, in ionization mode FAB,
It was measured by detecting positive ions.

Example 1 6-cyanomethyl-2,2-dimethyl-4H-1,3-
Synthesis of dioxin-4-one In a flask having a capacity of 20 ml, 6-chloromethyl-2,2
-Dimethyl-4H-1,3-dioxin-4-one 20
0 mg and 2.5 ml of dimethylformamide,
Dissolved. To this solution was added ammonium chloride 140.7.
mg and 293 mg of sodium cyanide were added, and the mixture was stirred at room temperature for 3 hours. The insolubles precipitated in the reaction solution were removed from water 5
ml was added and dissolved. Ethyl acetate 20m
The mixture was extracted twice with l, and the separated ethyl acetate phases were combined.

The obtained ethyl acetate phase was washed with saturated saline 10
After washing with ml, the solution was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The obtained residue is subjected to silica gel column chromatography (mobile phase: hexane / ethyl acetate =
The solution was purified by 1/1 (volume ratio) to obtain 47 mg of 6-cyanomethyl-2,2-dimethyl-4H-1,3-dioxin-4-one as a yellow liquid. The spectrum data of this compound is shown below. Note that methyl is sometimes referred to as Me.

IR (neat): 3000,2946,
2919, 2263, 1736, 1644 cm ^-1 .

¹ H-NMR (CDCl ₃ ) ppm: 1.74
(S, 6H, Me), 3.37 (s, 2H, CH 2 C
N), 5.52 (s, 1H, = CH).

¹³ C-NMR (CDCl ₃ ) ppm: 2
_{2.7 (NC- C H 2 -)} , 24.8 (C Me 2), 9
6.0 (HC =), 108.0 ( C Me 2), 112.
8 (-CN), 159.4, 159.5.

[0060] FAB-MS (m / z) : 168 (M + +
^{1,100%), 110 (M +} + 1-58,10%).

Example 2 Synthesis of ethyl 4-cyanoacetoacetate To 7.2 ml of chloroform was added 6-cyanomethyl-2,2.
-Dimethyl-4H-1,3-dioxin-4-one 30
mg and 32 mg of ethanol were dissolved and sealed in a sealed tube. The system was heated at 80 ° C. for 7 hours to react. When the ¹ H-NMR of the reaction solution was measured, the target 4-
Ethyl cyanoacetoacetate was produced in a yield of 93 mol%. ^{The 1} H-NMR spectrum data is shown below.

¹ H-NMR (CDCl ₃ ) ppm: 1.3
_{1 (t, 3H, -CH 2} -C H 3), 3.62 (s, 2
H, -C (= O) -CH 2 -C (= O) -), 3.71
(S, 2H, NC-CH 2 -C (= O) -), 4.24
_{(Q, 2H, -C H 2} -CH 3).

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C022 GA13 4H006 AA02 AC44 AC54 BA28 BA36 BA37 BA52 BB14 BB17 BB21 BB22 BC34 4H039 CA62 CA70 CH60

Claims (6)

[Claims] 1. A cyano compound represented by the following formula (1). Embedded image (Wherein, R ¹ and R ² are the same or different and represent a group capable of leaving together with an oxygen atom adjacent to the carbonyl group. R ¹
And R ² may form a ring with adjacent carbon atoms) 2. A formula (1), R ¹ and R ² are the same or different, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, or a heterocyclic group, R ¹ and R ²
The cyano compound according to claim 1, wherein the ring formed by is a cycloalkane ring or a heterocyclic ring. 3. A formula (1), R ¹ and R ² are the same or different, cyano compound of claim 1 wherein the C _1-6 alkyl group. 4. The method for producing a cyano compound according to claim 1, wherein the halogen compound represented by the following formula (2) is reacted with a cyanating agent. Embedded image (Wherein, X is a halogen atom, R ¹ and R ² are the same or different and represent a group capable of leaving together with an oxygen atom adjacent to the carbonyl group. R ¹ and R ² represent an adjacent carbon atom May form a ring together with 5. The method according to claim 4, wherein the reaction is carried out in the presence of at least one compound selected from an amine salt, an ammonium salt, an alkali metal halide and a cyclic polyether. 6. The cyano compound (1) according to claim 1,
Reacting with an alcohol or water represented by the following formula (3) R ³ OH (3) (wherein R ³ represents a hydrogen atom or a hydrocarbon group which may have a substituent), A method for producing a cyanoacetacetic acid derivative represented by the following formula (4). Embedded image (Wherein, R ³ is the same as described above)