Synthesis 1988; 1988(4): 274-277
DOI: 10.1055/s-1988-27541
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Highly Efficient Syntheses of Alkyl 3,3-Dialkoxypropanoates, Alkyl 4-Ethoxy-2-oxo-3-butenoates, and Monoprotected Malonaldehydes

Lutz-F. Tietze* , Heinrich Meier, Edgar Voß
  • *Institut für Organische Chemie der Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Federal Republic of Germany
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Publication History

Publication Date:
20 August 2002 (online)

Haloform reaction of 4-alkoxy-1,1,1-trichloro-3-buten-2-ones, which can be obtained by acylation of enol ethers, gives 3,3-dialkoxypropanoic esters. Transacetalization of ethyl 3,3-diethoxypropanoate with 2,2-dimethyl-1,3-propanediol, followed by reduction and oxidation with DMSO/oxalyl chloride yields a monoprotected malonaldehyde. 4-Ethoxy-2-oxo-3-butenoates are synthesized either by acylation of enol ethers with alkoxalyl chlorides or by Claisen condensation of alkyl pyruvates with orthoesters.