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Microwave-Assisted Aqueous Krapcho Decarboxylation

Jeremy D. Mason, S. Shaun Murphree*

*Department of Chemistry, Allegheny College, Meadville, PA 16335, USA, Email: smurphreallegheny.edu

J. D. Mason, S. S. Murphree, Synlett, 2013, 24, 1391-1394.

DOI: 10.1055/s-0033-1338701 (free Supporting Information)


Abstract

The Krapcho decarboxylation of alkyl malonate derivatives has been adapted to aqueous microwave conditions. For salt additives, 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 as co-solvent.

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Key Words

cleavage, decarboxylation, esters, hydrolysis, lithium, solvent effects, microwave synthesis


ID: J60-Y2013