Tuesday, August 27, 2019

organic chemistry - Can a benzyl ether be removed in the presence of an ester?


I'd like to deprotect a benzyl group for a Fráter–Seebach alkylation. Would it be possible to do this with a Birch reduction using Li/NH3 (or Na/NH3), without also reducing the ester carbonyl group?


Selective debenzylation of methyl (S)-3-(benzyloxy)butanoate



If not, hydrogenation over Pd/C seems to be a plausible alternative. How else can I remove the benzyl group on oxygen?




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