Sodium borohydride → 1-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

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Reaction Steps

To a solution of 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-93, 12.1 g, 39 mmol) in ethanol (250 mL) was added sodium borohydride (741 mg, 19.5 mmol). After heating to reflux for 2 h the mixture was cooled to room temperature, quenched with 10% HCl and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a colorless syrup. The material was used in the next step without further purification.

Provenance & Evidence