JP2000256371A - Production of 2-pyridylsilane derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for producing a 2-pyridylsilane derivative capable of easily being purified. SOLUTION: A 2-pyridylsilane derivative of formula I (wherein, R1 and R2 are each an alkyl group, or the like; R3-R6 are each H, a halogen, an alkyl group, or the like; R7 is ethyl group or vinyl one which may have a substituent at their 2-position) is produced by reacting a 2-pyridylsilane compound of formula II with 1-alkenes or 1-alkynes in the presence of a transition metal complex catalyst.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a 2-pyridylsilane derivative.

[0002]

2. Description of the Related Art A 2-pyridylsilane derivative has a silyl group which can be easily converted into another functional group, and is useful as a synthetic intermediate for various medical and agricultural chemicals, chemical products and the like. Moreover,
Since it has a pyridyl group, it can be purified by a general-purpose separation and purification method such as acid / base extraction, and the synthesis process using a 2-pyridylsilane derivative has a low environmental load. Process. further,
In recent years, research on automation of synthesis reactions has been advanced.
The pyridylsilane derivative is also useful as a substrate for a liquid-phase automatic synthesis reaction because it can be easily separated and purified. However, a simple method for synthesizing 2-pyridylsilanes has not been known.

[0003]

SUMMARY OF THE INVENTION
The present inventors have conducted intensive studies on a novel method for producing a 2-pyridylsilane derivative and arrived at the present invention.

[0004]

That is, the present invention relates to a compound of the general formula (2) in the presence of a transition metal complex catalyst. (Wherein, R ¹ and R ² are the same or different and each represents an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group or a trisubstituted silyl group; R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different and are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group, a cyano group, a nitro group, a hydroxyl group, an alkylsulfonyl group , An arylsulfonyl group or a trisubstituted silyl group, wherein the alkyl group, the alkoxy group, the aryl group,
The aryloxy group, aralkyl group, and aralkyloxy group may have a substituent. Wherein the 2-pyridylsilane compound represented by the formula) is reacted with a 1-alkene or 1-alkyne. (In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above, and R ⁷ is an ethyl group or vinyl optionally having a substituent at the 2-position. A method for producing a 2-pyridylsilane derivative represented by the formula:

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The starting material of the present invention is represented by the following general formula (2) In the formula of the 2-pyridylsilane compound represented by R ¹ and R ² are the same or different, and each represents an alkyl group,
Represents an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group or a trisubstituted silyl group, wherein R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different and are each a hydrogen atom, a halogen atom, an alkyl Represents a group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group, a cyano group, a nitro group, a hydroxyl group, an alkylsulfonyl group, an arylsulfonyl group or a trisubstituted silyl group. Here, the above-mentioned alkyl group, alkoxy group, aryl group, aryloxy group,
The aralkyl group and the aralkyloxy group may have a substituent.

Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, n-amyl,
Neopentyl group, n-hexyl group, cyclohexyl group, n
-Octyl group, n-nonyl group, menthyl group, 2,3,4
-Trimethyl-3-pentyl group, 2,4-dimethyl-3
A linear, branched or cyclic alkyl group having 1 to 12 carbon atoms such as a pentyl group; These alkyl groups are
For example, methoxy, ethoxy, n-propoxy, t-
1 carbon atom such as a butoxy group and a 1-methylheptyloxy group
To 12 alkoxy groups, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; an alkoxycarbonyl group having 2 to 8 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group and a t-butoxycarbonyl group, and benzyloxycarbonyl. Aralkyloxycarbonyl group such as group, aryloxycarbonyl group such as phenoxycarbonyl group, cyano group, nitro group or hydroxyl group, etc., and an alkyl group having such a substituent includes, for example, 3-chloropropyl group , 1-hydroxycyclohexyl group and the like.

The aralkyl group includes, for example, benzyl, 1-phenylethyl, 2-phenylethyl, 3
An alkyl group substituted with an aryl group such as a phenyl group such as a -phenylpropyl group, a 2-naphthylethyl group or a diphenylmethyl group, or a naphthyl group. These aralkyl groups may be substituted with the above-mentioned alkyl group, alkoxy group, halogen atom, alkyloxycarbonyl group, cyano group, nitro group, hydroxyl group, or the like.Examples of the aralkyl group having such a substituent include α- Examples include a hydroxybenzyl group, a 1-hydroxy-3-phenylpropyl group, a 1-hydroxy-1-phenylethyl group, and the like.

Examples of the alkoxy group include the same as the above-mentioned alkoxy group, and examples of the aryloxy group include those composed of an aryl group such as a phenyl group and a naphthyl group and an oxygen atom, for example, a phenoxy group and the like. Examples of the aralkyloxy group include those composed of the above-described aralkyl group and an oxygen atom, such as a benzyloxy group.

As the alkylsulfonyl group, for example, a methylsulfonyl group, an ethylsulfonyl group, etc.
Examples of the alkylsulfonyl group of No. 6 and the arylsulfonyl group include a phenylsulfonyl group and a p-tolylsulfonyl group. Examples of the trisubstituted silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a dimethylphenylsilyl group, a diphenylmethylsilyl group, a trimethoxysilyl group, a triphenoxysilyl group, and a dimethyl (2-pyridyl) silyl group. And the like.

The 2-pyridylsilane compound represented by the general formula (2) includes, for example, dimethyl (2-pyridyl) silane, dimethyl (5-methyl-2-pyridyl) silane, dimethyl (6-methyl-2-pyridyl) ) Silane,
Dimethyl (4-t-butyl-2-pyridyl) silane, dimethyl (4-phenyl-2-pyridyl) silane, dimethyl (4-methoxy-2-pyridyl) silane, dimethyl [6- (1-methylheptyl) oxy- 2-pyridyl]
Silane, dimethyl (3-benzyloxy-2-pyridyl) silane, dimethyl (3-fluoro-2-pyridyl)
Silane, dimethyl (4-cyano-2-pyridyl) silane, dimethyl (4-phenylsulfonyl-2-pyridyl) silane, dimethyl [6- (1,3-dioxolane-
2-yl) -2-pyridyl] silane and the like.

Examples of the transition metal complex catalyst include Group 8 and 9
Examples of the catalyst include a catalyst composed of a transition metal of Group 10 or Group 10 and a ligand. Examples of the transition metal of Group 8 include ruthenium and the like. Examples of the transition metal of Group 9 include rhodium and iridium. Examples of the transition metal include palladium and platinum.

Examples of the ligand include halogen atoms such as chlorine atom, bromine atom and iodine atom, phosphine-based ligands such as triphenylphosphine, triethylphosphine and diphenylphosphinopropane, ethylene, cyclopentadiene and pentamethylcyclohexane. Pentadiene, 1,5-
Olefin-based ligands such as cyclooctadiene and norbornadiene are exemplified.

Examples of the transition metal complex catalyst include a palladium complex catalyst such as tetrakis (triphenylphosphine) palladium (0), chlorotris (triphenylphosphine) rhodium (I), and cyclopentadienylbis (triphenylphosphine). Rhodium-based complex catalysts such as rhodium (I) and bis (cyclooctadiene) diiododirhodium (I), chloro (cyclopentadienyl) bis (triphenylphosphine) ruthenium (II), chloro (pentamethylcyclopentadienyl) ) (1,3-bis (diphenylphosphino) propane) ruthenium (II), chloro (pentamethylcyclopentadienyl) (1,5-cyclooctadiene) ruthenium (II), dichlorotris (triphenylphosphine) ruthenium (II) Ruthenium-based complex catalyst,
Iridium-based complex catalysts such as chlorotris (triphenylphosphine) iridium (I) and pentamethylcyclopentadienylbis (ethylene) iridium (I);
(Ethylene) bis (triphenylphosphine) platinum (0), trans- [chloro (ethyl) bis (triethylphosphine) platinum (II)], cis- [diethylbis (triethylphosphine) platinum (II)], dichloro (norbornadiene) Platinum-based complex catalysts such as platinum (II), tetrakis (triphenylphosphine) platinum (0), (cyclooctadiene) bis (triphenylphosphine) platinum (0), etc., and rhodium in terms of reactivity and the like. Complex catalysts and platinum complex catalysts are preferred, and rhodium complex catalysts are particularly preferred.

The amount of the transition metal complex catalyst used is usually 0.001 to 10 mol%, preferably 0.01 to 10 mol% based on the 2-pyridylsilane compound represented by the general formula (2).
５5 mol%.

The 1-alkene or 1-alkyne to be reacted with the 2-pyridylsilane compound represented by the general formula (2) includes, for example, 1-propene, 1-hexene,
1-octene, methyl acrylate, methyl 3,3-
Dimethylpentanoate-4-ene, styrene, 3-chlorostyrene, allylphenyl ether, 2-allylphenol, vinylcyclopentane, allylcyanide,
-Pentin, 1-octyne, 3,3-dimethyl-1-butyne, cyclopentylacetylene, phenylacetylene, 1-ethynyl-1-cyclohexanol, propargyl alcohol, methylpropiolate, methylpropargyl ether and the like.

The amount of the 1-alkene or 1-alkyne used is usually 0.5 mole times or more, preferably 1 mole times, based on the 2-pyridylsilane compound represented by the general formula (2). The upper limit is not particularly limited, but is usually 5 mol times or less, preferably 2 mol times or less in consideration of economical aspects.

The reaction between the 2-pyridylsilane compound represented by the general formula (2) and 1-alkenes or 1-alkynes is usually carried out in a solvent, for example, methanol, ethanol, i-propanol. Alcohol solvents, such as diethyl ether, t-butyl methyl ether, di (n-butyl) ether, tetrahydrofuran, etc., ester solvents such as ethyl acetate, n
-Hexane, n-heptane, aliphatic hydrocarbon solvents such as cyclohexane, benzene, toluene, aromatic hydrocarbon solvents such as xylene, chloroform, dichloromethane,
Examples include halogenated hydrocarbon solvents such as dichloroethane and chlorobenzene, and mixed solvents thereof. The amount of the solvent used is not particularly limited. The reaction temperature is usually 0
C. to the boiling point of the reaction mixture.

The 2-pyridylsilane derivative represented by the general formula (1) thus obtained can be taken out of the reaction mixture with high purity by subjecting the reaction mixture to the following treatment without subjecting it to separation and purification treatments such as column chromatography. it can. Of course, the 2-pyridylsilane derivative represented by the general formula (1) may be further purified by, for example, column chromatography.

An acidic aqueous solution and, if necessary, a hydrophobic organic solvent are added to the reaction mixture to effect acidification and liquid separation to form an aqueous layer containing the 2-pyridylsilane derivative represented by the general formula (1). obtain. The aqueous layer is treated with an alkali and extracted with a hydrophobic organic solvent to obtain an organic layer containing a 2-pyridylsilane derivative represented by the general formula (1), and the organic layer is concentrated.

As the acidic aqueous solution, an aqueous solution of a mineral acid such as hydrochloric acid or sulfuric acid is usually used. Examples of the hydrophobic organic solvent include alcohol solvents having 4 or more carbon atoms such as butanol and hexanol, ketone solvents having 4 or more carbon atoms such as methyl ethyl ketone and methyl isobutyl ketone, diethyl ether, t-butyl methyl ether, and di (n Ether solvents such as -butyl) ether and tetrahydrofuran; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as n-hexane, n-heptane and cyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene and xylene. Solvents, halogenated hydrocarbon solvents such as chloroform, dichloromethane, dichloroethane, chlorobenzene and the like, and mixed solvents thereof and the like. Examples of the alkali used in the alkali treatment include sodium hydroxide, potassium hydroxide, potassium carbonate and the like, and these are used as they are or as an aqueous solution.

The 2-pyridylsilane derivative represented by the general formula (1) thus obtained includes, for example, dimethyl (1-propyl) (2-pyridyl) silane, dimethyl (1-hexyl) (2-pyridyl) silane, dimethyl (1-octyl) (2-pyridyl) silane, dimethyl (2-methoxycarbonylethyl) (2-pyridyl) silane, dimethyl (4-methoxycarbonyl-3,3-dimethylbutyl) (2-pyridyl) silane, dimethyl ( 2
-Phenylethyl) (2-pyridyl) silane, dimethyl [2- (4-chlorophenyl) ethyl] (2-pyridyl) silane, dimethyl (3-phenoxypropyl) (2
-Pyridyl) silane, dimethyl [3- (2-hydroxyphenyl) propyl] (2-pyridyl) silane, dimethyl (2-cyclopentylethyl) (2-pyridyl) silane, dimethyl (3-cyanopropyl) (2-pyridyl)
Silane, dimethyl (1-pentenyl) (2-pyridyl)
Silane, dimethyl (1-octenyl) (2-pyridyl)
Silane, dimethyl (3,3-dimethyl-1-butenyl)
(2-pyridyl) silane, dimethyl (2-cyclopentylvinyl) (2-pyridyl) silane, dimethyl (2-phenylvinyl) (2-pyridyl) silane, dimethyl [2
-(1-hydroxycyclohexyl) vinyl] (2-pyridyl) silane, dimethyl (3-hydroxy-1propenyl) (2-pyridyl) silane, dimethyl (2-methoxycarbonylvinyl) (2-pyridyl) silane, dimethyl (3 -Methoxy-1-propenyl) (2-pyridyl)
Silane, dimethyl (1-propyl) (5-methyl-2-
Pyridyl) silane, dimethyl (1-hexyl) (6-methyl-2-pyridyl) silane, dimethyl (1-octyl) (4-t-butyl-2-pyridyl) silane, dimethyl (1-octyl) (4-phenyl -2-pyridyl) silane, dimethyl (1-octyl) (4-methoxy-2-
Pyridyl) silane, dimethyl (1-octyl) (3-benzyloxy-2-pyridyl) silane, dimethyl (1-
Octyl) (3-fluoro-2-pyridyl) silane, dimethyl (1-octyl) (4-cyano-2-pyridyl)
Silane, dimethyl (1-octyl) (4-phenylsulfonyl-2-pyridyl) silane and the like.

It should be noted that the obtained 2 represented by the general formula (1)
By reacting the pyridylsilane derivative with, for example, a peroxide, the silicon-carbon bond is oxidatively cleaved and can be easily converted to alcohols. When R ^{7 in} the formula (1) is a vinyl group which may have a 2-position substituent, aldehydes isomerized into a more stable structure are obtained.

Further, a 2-pyridylsilane derivative can be produced by the method of the present invention, and the 2-pyridylsilane derivative can be subjected to other reactions, for example, an alkylation reaction such as methylation, a reduction reaction, and the like. The obtained reaction product and the like can be easily separated and purified by subjecting the reaction mixture to a general-purpose acid / base extraction treatment.

[0024]

According to the present invention, it is possible to easily produce a 2-pyridylsilane derivative which can be purified by a general-purpose separation / purification method called acid / base extraction. Therefore, the production method of the present invention is applicable to, for example, a liquid phase automatic synthesis reaction.

[0025]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. The following examples were all performed in an argon atmosphere.

Example 1 166 mg (1.5 mmol) of 1-octene and chlorotris (triphenylphosphine) rhodium (I) 23
mg (0.25 μmol) in acetonitrile 0.6 ml
Was dissolved. 69 mg (0.5 mmol) of dimethyl (2-pyridyl) silane was added dropwise to this solution over 1 hour at room temperature. After completion of the dropwise addition, the mixture was stirred and maintained at room temperature for 30 minutes, and then 6 ml of 1N hydrochloric acid and 5 ml of diethyl ether were added.
After stirring for another 30 minutes, the layers were separated. After the organic layer was extracted five times with 6 ml of 1N hydrochloric acid, the obtained aqueous layers were mixed and made basic by adding sodium hydroxide in the form of pellets. The mixture was extracted three times with 10 ml of diethyl ether. The obtained organic layer was dried over potassium carbonate, the solvent was removed under reduced pressure, and dimethyl (1-octyl) (2-
107 mg of pyridyl) silane were obtained (86% yield, NM).
R and GC purity> 95%).

¹ H-NMR (CDCl ₃ , 500 MH
z): δ / ppm 0.30 (s, 6H), 0.80
−0.84 (m, 2H), 0.86 (t, J = 7.1)
Hz, 1H), 1.20-1.37 (m, 12H),
7.18 (ddd, J = 7.7, 5.0, 1.5H
z, 1H), 7.48 (dt, J = 7.7, 1.5H
z, 1H), 7.57 (td, J = 7.7, 1.5H
z, 1H), 7.77 (dt, J = 5.0, 1.5H
z, 1H) ¹³ C-NMR (CDCl ₃ , 125 MHz): δ / pp
m-3.6, 14.1, 14.8, 22.6,
23.7, 29.22, 29.23, 31.
9, 33.5, 122.6, 129.0, 13
3.8, 150.1, 168.0

Example 2 10 mg (0.25 μmol) of bis (cyclooctadiene) platinum, 13 mg (0.50 μmol) of triphenylphosphine and 165 mg (1.5 mmol) of 1-octyne were added to 1.0 ml of diethyl ether.
At room temperature, 69 mg (0.5 mmol) of dimethyl (2-pyridyl) silane was added dropwise over 1 hour. Further, after stirring and holding at an internal temperature of 40 ° C. for 6 hours, 6 ml of 1N hydrochloric acid and 5 ml of diethyl ether were added, and the mixture was stirred for 30 minutes, allowed to stand, and separated. The organic layer was extracted five times with 6 ml of 1N hydrochloric acid, the obtained aqueous layers were mixed, and sodium hydroxide in the form of pellets was added to make the mixture basic. This was extracted three times with 10 ml of diethyl ether. The obtained organic layer was dried over magnesium sulfate, the solvent was removed under reduced pressure, and 112 mg of dimethyl (1-octenyl) (2-pyridyl) silane was obtained.
I got 90% yield.

Reference Example 1 After 121 mg (2.09 mmol) of potassium fluoride and 204 mg (2.04 mmol) of potassium hydrogen carbonate were dissolved in a mixed solvent of 2.5 ml of methanol and 2.5 ml of tetrahydrofuran, the same method as in Example 1 was used. The obtained dimethyl (1-octyl) (2-pyridyl) silane 2
46 mg (0.99 mmol) and 3.47 g (30.4 mmol) of 30% aqueous hydrogen peroxide were added. The mixed solution was stirred and maintained at an internal temperature of 50 ° C. for 12 hours. Thereafter, the mixture was cooled to room temperature, 20 ml of water was added to the solution, and the mixture was extracted five times with 20 ml of diethyl ether. The obtained organic layers were mixed, washed with 20 ml of 15% sodium thiosulfate, dried over sodium sulfate, and then the solvent was removed under reduced pressure to obtain 1-octanol (yield 82%).

Reference Example 2 Methyl 3,3-dimethylpentanoate-4-ene 2
13 mg (1.5 mmol) and 23 mg of chlorotris (triphenylphosphine) rhodium (I) (0.
25 μmol) in 0.2 ml of acetonitrile,
69 mg (0.5 mmol) of dimethyl (2-pyridyl) silane was added dropwise to this solution over 1 hour at room temperature. After the completion of the dropwise addition, the mixture was stirred and maintained at room temperature for 1 hour, and then added with 1N hydrochloric acid 6
Then, 2 ml of diethyl ether and 2 ml of diethyl ether were added, and the mixture was further stirred for 30 minutes and then separated. The obtained organic layer was washed with 1N hydrochloric acid (6 ml).
After extracting twice with water, the obtained aqueous layers were mixed, neutralized with sodium hydroxide in the form of pellets, and diethyl ether was added.
Extraction was performed three times with 0 ml. After the organic layer was dried over magnesium sulfate, the solvent was removed under reduced pressure to obtain 116 mg of dimethyl (4-methoxycarbonyl-3,3-dimethylbutyl) (2-pyridyl) silane as a colorless oil. (83% yield,> 95% purity).

¹ H-NMR (CDCl ₃ , 300 MH
z): δ / ppm 0.24 (s, 6H), 0.66
−0.74 (m, 2H), 0.87 (s, 6H),
1.20-1.30 (m, 2H), 2.11 (s, 2
H), 3.52 (s, 3H), 7.11 (ddd, J
= 7.5, 4.8, 1.5 Hz, 1H), 7.42
(Ddd, J = 7.5, 1.5, 0.9 Hz, 1H
z), 7.50 (td, J = 7.5, 1.5 Hz, 1
H), 8.69 (ddd, J = 4.8, 1.2, 0.
9 Hz, 1 H) ¹³ C-NMR (CDCl ₃ , 75 MHz): δ / ppm
-4.1, 8.4, 26.6, 33.9, 3
5.8, 44.9, 50.9, 122.7, 1
29.1, 133.9, 150.2, 167.
6, 173.0

To 40 mg (143 μmol) of the obtained dimethyl (4-methoxycarbonyl-3,3-dimethylbutyl) (2-pyridyl) silane was added 1 ml of diethyl ether.
Was added to form a solution, and a methyllithium / diethyl ether solution (716 μmol) was added dropwise to the solution at an internal temperature of 0 ° C. After completion of the dropwise addition, the mixture was stirred at an internal temperature of 0 ° C for 1 hour,
5 ml of hydrochloric acid were added. Furthermore, stirring is performed at an internal temperature of 0 ° C. for 30 minutes,
After holding, liquid separation was performed, and the obtained organic layer was diluted with 1N hydrochloric acid (10 m).
The extraction was performed three times with l. The obtained aqueous layers were mixed, made basic by adding sodium hydroxide in the form of pellets, and extracted twice with 10 ml of diethyl ether. After drying the organic layer over magnesium sulfate, the solvent was removed under reduced pressure to obtain 37 mg of dimethyl (5-hydroxy-3,3-dimethylhexyl) (2-pyridyl) silane as a colorless oil (yield 93%). Purity> 95%).

¹ H-NMR (CDCl ₃ , 300 MH
z): δ / ppm 0.27 (s, 6H), 0.77
−0.84 (m, 2H), 0.94 (s, 6H),
1.24 (s, 6H), 1.30-1.38 (m, 2
H), 1.49 (s, 2H), 2.34 (brs, 1
H), 7.17 (ddd, J = 7.5, 4.8, 1.
5 Hz, 1 H), 7.47 (ddd, J = 7.5,
1.5, 1.2 Hz, 1 Hz), 7.56 (td, J
= 7.5, 1.8 Hz, 1H), 8.73 (ddd,
J = 4.8, 1.8, 1.2 Hz, 1H) ¹³ C-NMR (CDCl ₃ , 75 MHz): δ / ppm
-3.7, 8.3, 28.6, 31.7, 3
4.4, 37.1, 52.0, 72.0, 12
2.8, 129.2, 134.1, 150.0,
167.8

Potassium fluoride 69 mg (1.18 mmol
l) and 118 mg of potassium hydrogen carbonate (1.18 mo
l) was dissolved in 1 ml of methanol, and 165 mg (590 μmo) of dimethyl (5-hydroxy-3,3-dimethylhexyl) (2-pyridyl) silane obtained in the same manner as above in 1.5 ml of tetrahydrofuran.
l) Dissolved solution and 2.0 g of 30% hydrogen peroxide solution
(17.7 mol) was added. After mixing the solution, the internal temperature 5
After stirring and maintaining at 0 ° C. for 22 hours, the mixture was cooled to room temperature.
After adding 10 ml of water to the solution after the reaction, the mixture was extracted three times with 20 ml of diethyl ether, and the obtained organic layers were mixed.
After washing with 20 ml of 15% sodium thiosulfate and drying over magnesium sulfate, the solvent was removed under reduced pressure.
4,4-Trimethyl-2,6-hexanediol was obtained. This was purified by a silica gel column with a mixed solvent of hexane / ethyl acetate = 1/1 (volume ratio) to obtain 94 mg of 2,4,4-trimethyl-2,6-hexanediol as a colorless oil (yield: 99). %, Purity> 95%).

 ──────────────────────────────────────────────────続 き Continued on front page F term (reference) 4H039 CA19 CA29 CA42 CA92 CF10 CF20 4H049 VN01 VP01 VQ59 VR24 VS59 VT17 VT30 VT45 VU01 VU04 VU06 VU36 VV13 VW02 VW32

Claims (6)

[Claims] 1. A compound of the formula (2) in the presence of a transition metal complex catalyst (Wherein, R ¹ and R ² are the same or different and each represents an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group or a trisubstituted silyl group; R ³ , R ⁴ , R ⁵ and R ⁶ are the same or different and are each a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, an aralkyloxy group, a cyano group, a nitro group, a hydroxyl group, an alkylsulfonyl group , An arylsulfonyl group or a trisubstituted silyl group, wherein the alkyl group, the alkoxy group, the aryl group,
The aryloxy group, aralkyl group, and aralkyloxy group may have a substituent. Wherein the 2-pyridylsilane compound represented by the formula) is reacted with a 1-alkene or 1-alkyne. (In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above, and R ⁷ is an ethyl group or vinyl optionally having a substituent at the 2-position. A 2-pyridylsilane derivative represented by the formula: 2. The method for producing a 2-pyridylsilane derivative according to claim 1, wherein the transition metal complex catalyst is a catalyst comprising a Group 8, 9, or 10 transition metal and a ligand. . 3. The method for producing a 2-pyridylsilane derivative according to claim 2, wherein the Group VIII transition metal is ruthenium. 4. The method for producing a 2-pyridylsilane derivative according to claim 2, wherein the Group 9 transition metal is rhodium or iridium. 5. The method for producing a 2-pyridylsilane derivative according to claim 2, wherein the Group 10 transition metal is palladium or platinum. 6. The method for producing a 2-pyridylsilane derivative according to claim 2, wherein the ligand is at least one selected from the group consisting of a halogen atom, a phosphine-based ligand, and an olefin-based ligand.