Synlett 2013; 24(11): 1391-1394
DOI: 10.1055/s-0033-1338701
letter
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Aqueous Krapcho Decarboxylation

Jeremy D. Mason
Department of Chemistry, Allegheny College, Meadville, PA 16335, USA   Fax: +1(814)3322789   Email: smurphre@allegheny.edu
,
S. Shaun Murphree
Department of Chemistry, Allegheny College, Meadville, PA 16335, USA   Fax: +1(814)3322789   Email: smurphre@allegheny.edu
› Author Affiliations
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Publication History

Received: 24 March 2013

Accepted after revision: 11 April 2013

Publication Date:
08 May 2013 (online)


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Abstract

The Krapcho decarboxylation of alkyl malonate derivatives has been adapted to aqueous microwave conditions. Various salt additives were examined, and both the cation and the anion impacted the facility of the reaction. A strong correlation was found between the pKa of the anion and the reaction rate, suggesting a straightforward base-catalyzed hydrolysis. Lithium sulfate gave the best results, obviating the need for DMSO co-solvent.

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