Ethyl Acetate → 3-Methyl-2-(tert-butyldimethylsilyloxy)-1-butanol

Participants

Reaction Steps

A stirred, ice-cooled solution of 3-methyl-2-(tert-butyldimethylsilyloxy)butanal (Preparation 7) (0.5 g) in THF (4 ml) and ethanol (8 ml) was treated with sodium borohydride (0.1 g). After 20 minutes, the reaction mixture was worked-up (ethyl acetate) to give the intermediate 3-methyl-2-(tert-butyldimethylsilyloxy)-1-butanol as an oil. This was dissolved in dichloromethane (5 ml), cooled to 0° C., and treated with pyridine (0.5 ml) and trifluoromethansulphonic anhydride (0.5 ml). After stirring for 1 hour, the reaction mixture was worked-up (ether) to give the title compound as an oil.

Provenance & Evidence