反応 #310900

反応方程式

trans-2-(chloromethyl)cyclohexanenitrile

Sodium ethylate

sodium

ethyl 2-(3-mercaptophenyl)propionate

→

ethyl 2-[3-(2-cyanocyclohexylmethylthio)phenyl]propionate

収率 78.5%

溶媒

ethanol

反応条件

後処理

1. 1
   温度the resulting mixture was refluxed for 5 hours in an oil bath
2. 2
   その他The reaction mixture was evaporated to dryness under reduced pressure and to the residue
3. 3
   workup.ADDITIONwas added toluene
4. 4
   その他After removal of the insoluble material
5. 5
   ろ過by filtration
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   その他The residue was chromatographed on silica gel

実験手順

Sodium ethylate prepared from sodium (0.23 g) and ethanol (10 ml) was added to ethyl 2-(3-mercaptophenyl)propionate (2.10 g) and the mixture was stirred for a while. Thereto was added trans-2-(chloromethyl)cyclohexanenitrile (1.58 g) and the resulting mixture was refluxed for 5 hours in an oil bath maintained at 100° C. The reaction mixture was evaporated to dryness under reduced pressure and to the residue was added toluene. After removal of the insoluble material by filtration, the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel, using chloroform as an eluent, to give ethyl 2-[3-(2-cyanocyclohexylmethylthio)phenyl]propionate (2.6 g) as an oil. IRνmaxfilm cm-1 : 2230 (C≡N), 1720 (C=O). MS m/e: 331 (M+).

出典