Diethyl Ether → 3-(S)-methyl-5-(t-butyldimethylsilyloxy)-1-pentanol

Participants

Reaction Conditions

Reaction Steps

To 8.5 g. (0.224 m) of lithium aluminum hydride in 250 ml. of diethyl ether under nitrogen was added 53.5 g. (0.206 m) of methyl 3-(R)-methyl-5-(t-butyldimethylsilyloxy)pentanoate in 125 ml. of ether. The reaction was stirred for one hour at 0° C. and was then treated dropwise with 8.4 g. of water, 8.4 ml. of a 15% sodium hydroxide solution and 25.2 ml. of water. The solids were filtered and the organic phase separated and washed with water, 2.5% hydrochloric acid and a brine solution. The organic phase was dried over magnesium sulfate and concentrated in vacuo to give 46 g. of product.

Provenance & Evidence