Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

  • Beilstein J Org Chem. 2011:7:1323-6. doi: 10.3762/bjoc.7.155.
Anne T Hylden  1 ,  Eric J Uzelac ,  Zeljko Ostojic ,  Ting-Ting Wu ,  Keely L Sacry ,  Krista L Sacry ,  Lin Xi ,  T Nicholas Jones
Affiliations
  • 1. Department of Chemistry, College of St. Benedict, St. John's University, St. Joseph, MN 56374, USA.
PMID: 22043242 DOI: 10.3762/bjoc.7.155
Abstract

The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58-90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

Keywords
Lewis acids; acyl chlorides; alcohols; alkynes; cyclization.
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