Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


see article for more reactions

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.

see article for more examples



Key Words

Trifluoromethyl Ketones, Decarboxylation


ID: J42-Y2008-3770