ethyl (S)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate → (S)-alpha-(t-Butyldimethylsilyloxy)-alpha-phenylacetaldehyde

Participants

Reaction Steps

Following a procedure similar to that described in Preparation 25, but using 8.8 g of ethyl (S)-α-(t-butyldimethylsilyloxy)-α-phenylacetate (prepared as described in Preparation 24), 300 ml of dry hexane and 30 ml of a 1M solution of diisobutylaluminum hydride in hexane, and then purifying the reaction product by column chromatography through silica gel, using a 1:60 by volume mixture of ethyl acetate and hexane as the eluent, the title compound was obtained having an Rf=0.29 (thin layer chromatography over silica gel, using a 1:80 by volume mixture of ethyl acetate and hexane as the developing solvent).

Provenance & Evidence