반응 #65692

반응 방정식

2,3,4,5-tetrahydro-3,3-dimethyl-benzothiepin-7-yl methyl ketone

ethyl α-(diethoxyphosphinyl)-p-toluate

sodium hydride

hydrogen

→

ethyl p-[(E)-2-(2,3,4,5-tetrahydro-3,3-dimethyl-1-benzothiepin-7-yl)propenyl]benzoate

용매

dimethylformamide

반응 조건

후처리

1. 1
   추출extracted with ether
2. 2
   세척the ethereal solution was washed with water
3. 3
   기타dried
4. 4
   기타evaporated
5. 5
   기타Chromatography on silica gel (petroleum ether/ethyl acetate (95:5)) and recrystallization from hexane

실험 절차

8.85 g of ethyl α-(diethoxyphosphinyl)-p-toluate were slowly added dropwise to 1.3 g of sodium hydride (50% in mineral oil) in 28 ml of dimethylformamide. The reaction mixture was stirred at room temperature until the evolution of hydrogen had finished. Thereafter, 4.2 g of 2,3,4,5-tetrahydro-3,3-dimethyl-benzothiepin-7-yl methyl ketone were added and the reaction mixture was stirred at room temperature for 2 hours. Thereafter, the mixture was poured on to ice/sodium chloride, extracted with ether, the ethereal solution was washed with water and dried and evaporated. Chromatography on silica gel (petroleum ether/ethyl acetate (95:5)) and recrystallization from hexane yielded ethyl p-[(E)-2-(2,3,4,5-tetrahydro-3,3-dimethyl-1-benzothiepin-7-yl)propenyl]benzoate of melting point 96°-97° C.

출처