Boron tribromide → 1-(3-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

Participants

Reaction Steps

To 1-(3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-86, 14.2 g, 61.2 mmol) in dichloromethane (350 mL) at −78° C. was added boron tribromide (1 M in hexane, 80 mL, 80 mmol). After stirring from −78° C. to room temperature over 3 h the reaction mixture was quenched with sodium bicarbonate at −10° C. and extracted with diethyl ether. Combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from diethyl ether afforded the title compound as a brown solid.

Provenance & Evidence