4.4 Article

Microwave-Assisted Aqueous Krapcho Decarboxylation

Journal

SYNLETT
Volume 24, Issue 11, Pages 1391-1394

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1338701

Keywords

cleavage; esters; hydrolysis; lithium; solvent effects

Funding

  1. Allegheny College (Shanbrom Fund)
  2. Petroleum Research Fund [PRF 42382-B1]
  3. National Science Foundation [CCLI 0837640]

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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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