반응 #52344

반응 방정식

6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

→

title compound

수율 52.0%

6-Hydroxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one

수율 52.0%

용매

boron tribromide

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to −78° C.
2. 2
   기타quenched
3. 3
   workup.ADDITIONdiluted with saturated aqueous sodium bicarbonate solution
4. 4
   추출the aqueous phase was extracted with dichloromethane (×2)
5. 5
   건조The combined organic phase was dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated in vacuo to an oil

실험 절차

A stirred, cooled (−78° C.) solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalene-1-one Intermediate 9, 0.8, 3 mmol) under argon was treated with a 1M solution of boron tribromide (10 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was cooled to −78° C., quenched and diluted with saturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with dichloromethane (×2). The combined organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 30% ethyl acetate in hexane as the eluent afforded the title compound (0.3 g, 52%) as a yellow viscous oil.

출처