Synthesis 1990; 1990(1): 43-47
DOI: 10.1055/s-1990-26783
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Eine flexible Synthese von 4-Oxobutansäure- methylestern und deren Derivaten

Thomas Kunz* , Agnes Janowitz, Hans-Ulrich Reißig
  • *Institut für Organische Chemie der Technischen Hochschule Darmstadt, Petersenstraße 22, D-6100 Darmstadt, Federal Republic of Germany
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Publication History

Publication Date:
17 September 2002 (online)

A Flexible Synthesis of Methyl 4-Oxobutanoates and Their Derivatives Ring cleavage of several methyl 2-trimethylsiloxycyclopropanecarboxylates 3 provides rather sensitive methyl 4-oxobutanoates (ß-formyl esters) 4 in excellent yields. Siloxycyclopropanes 3 are easily available either directly from the corresponding silyl enol ethers 2 and methyl diazoacetate or by alkylation of deprotonated cyclopropanes 3. A highly efficient one-pot procedure affords methyl 4,4-dimethoxybutanoates 5, which can be converted into protected 4-hydroxybutanals 7 and 8 by standard methods.