Trifluoromethyl Ketones from Enolizable Carboxylic Acids via Enediolate Trifluoroacetylation/Decarboxylation

Jonathan T. Reeves*, Jinhua J. Song, Zhulin Tan, Heewon Lee, Nathan K. Yee and Chris H. Senanayake

*Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Old Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, Email: jonathan.reevesboehringer-ingelheim.com

J. T. Reeves, J. J. Song, Z. Tan, H. Lee, N. K Yee, C. H. Senanayake, J. Org. Chem., 2008, 73, 9476-9478.

DOI: 10.1021/jo801737c

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Abstract

Enolizable carboxylic acids were converted in a single step to trifluoromethyl ketones. Treatment of the acid with LDA generated an enediolate that was trifluoroacetylated with EtO₂CCF₃. Quenching the reaction mixture with aqueous HCl resulted in rapid decarboxylation and provided the trifluoromethyl ketone product in good yield.

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Key Words

Trifluoromethyl Ketones, Decarboxylation

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ID: J42-Y2008-3770