Benzophenone → Benzyl acetate

Participants

Reaction Steps

For example, 1-cyclohexenyloxy-[((1-naphthyl)phenyl)methyl]dimethylsilane, which is a silyl enol ether form of cyclohexanone, may be formed by treating cyclohexanone with lithium diisopropylamide at low temperature (e.g. −78° C.) so as to generate a lithium enolate, and capturing this with [((1-naphthyl)phenyl)methyl]dimethylsilyl chloride. By the same method, a ketone having an active hydrogen such as acetone or benzophenone may be derivatized to the corresponding silyl enol ether. Furthermore, a silyl ketene acetal form of benzyl acetate may be formed by treating benzyl acetate with lithium diisopropylamide at low temperature (e.g. −78° C.) so as to generate a lithium enolate, and capturing this with [((1-naphthyl)phenyl)methyl]dimethylsilyl chloride. By the same method, a carboxylic acid ester having an active hydrogen may be derivatized to the corresponding silyl ketene acetal.

Provenance & Evidence