Reaktion #65692

Reaktionsgleichung

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

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ether
2. 2
   Waschenthe ethereal solution was washed with water
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated
5. 5
   SonstigeChromatography on silica gel (petroleum ether/ethyl acetate (95:5)) and recrystallization from hexane

Vorschrift

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.

Quelle