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Malonic Ester Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr407

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Malonic Ester Synthesis. Comprehensive Organic Name Reactions and Reagents. 407:1811–1815.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

It is a common reaction using dialkyl malonates, mostly diethyl malonate, as starting material, and is known as malonic ester synthesis. The reaction mechanism shows that the reaction proceeds via the participation of the α-methylene protons of dialkyl malonates, which usually undergo nucleophilic substitutions and nucleophilic additions. It has been found that the alkylation rate is related to the acidity of α-proton. During the alkylation of malonic acid ester, the reversible cleavage of formed alkyl malonic acid ester or dialkyl malonic acid ester gives a simple alkyl ester. These alkylated malonic acid esters are used to synthesize barbiturates. The reaction has been modified for traceless synthesis on solid support and after the desired reaction, one of the ester groups can be removed. This reaction has been found useful in organic synthesis.

Keywords:

  • diethyl malonate;
  • SN2 mechanism;
  • alkylated malonic acid esters;
  • β-ketoester