A One-Carbon Homologation of Carbonyl Compounds to Carboxylic Acids, Estersand Amides

Stephen E. Dinizo, Robert W. Freerksen, W. Edward Pabst, David S. Watt

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

An efficient sequence for the one-carbon homologation of aldehydes and ketones to carboxylic acids 2, esters 3and amides 4 involves (1) the Horner-Emmons modification of the Wittig reaction using diethyl tert-butoxy(cyano)methylphos-phonate (EtO)2POCH(CN)O-t-Bu to afford α-tert-butoxyacrylonitriles 15, (2) the cleavage of the tert-butyl ether in 15 using zinc chloride in refluxing acetic anhydride to afford α-acetoxyacrylonitriles 16and (3) the hydroxide, alkoxide, or amine solvolysis of 16 to afford 2, 3, or 4, respectively, in 57-88% overall yield from the carbonyl compounds.

Original languageEnglish
Pages (from-to)182-186
Number of pages5
JournalJournal of the American Chemical Society
Volume99
Issue number1
DOIs
StatePublished - 1977

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Biochemistry
  • Colloid and Surface Chemistry

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