반응 #74637

반응 방정식

water

sulphur trioxide

1-(diphenylmethyl)azetidin-3-ol hydrochloride salt

triethylamine

→

title compound

수율 67.0%

1-(diphenylmethyl)azetidin-3-one

수율 67.0%

용매

tetrahydrofuran

DMSO

반응 조건

후처리

1. 1
   추출extracted with (1:1) ethyl acetate
2. 2
   세척The combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml)
3. 3
   건조dried over anhydrous sodium sulphate
4. 4
   농축concentrated in vacuo
5. 5
   기타Crude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane

실험 절차

To a stirred solution of 1-(diphenylmethyl)azetidin-3-ol hydrochloride salt, (20 g, 72.5 mmol) in tetrahydrofuran (69 ml) and DMSO (173 ml) was added triethylamine (50.5 ml, 362.6 mmol) at 0° C. Then sulphur trioxide:pyridine complex (69 g, 433 mmol) was added portionwise to the reaction mixture over 10 minutes. The resulting yellow solution was stirred at room temperature for 2 hours. Then the reaction mixture was poured in to cold water (173 ml) and extracted with (1:1) ethyl acetate:hexane (5×200 ml). The combined organic layer was washed with water (200 ml), saturated aqueous sodium chloride solution (200 ml), dried over anhydrous sodium sulphate and concentrated in vacuo. Crude product was purified over 100-200 silica gel using 5% v/v ethyl acetate in hexane to get 11.4 g (67%) of the title compound as a white solid.

출처