Regioselective synthesis of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones by [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes

J Org Chem. 2007 Aug 3;72(16):6273-5. doi: 10.1021/jo070847e. Epub 2007 Jul 6.

Abstract

A variety of 5-alkylsalicylates, 5-alkyl-2-hydroxy-acetophenones, and 5-alkyl-2-hydroxy-benzophenones was regioselectively prepared by TiCl4 mediated formal [3 + 3] cyclization of 1,3-bis(silyl enol ethers) with 2-alkyl-1,1,3,3-tetraethoxypropanes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemical synthesis*
  • Acetophenones / chemistry
  • Alcohols / chemistry
  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry
  • Catalysis
  • Chemistry, Organic / methods*
  • Cyclization
  • Ethers / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Models, Molecular
  • Molecular Conformation
  • Propane / chemistry*
  • Salicylates / chemical synthesis*
  • Salicylates / chemistry
  • Stereoisomerism

Substances

  • Acetophenones
  • Alcohols
  • Benzophenones
  • Ethers
  • Salicylates
  • Propane