Alternative, high-yield synthesis of (E)-4-oxonon-2-enoic acid from 2-methoxyfuran


MARAŞ A. , ALTAY A., BALLINI R.

SYNTHETIC COMMUNICATIONS, vol.38, no.2, pp.212-216, 2008 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 38 Issue: 2
  • Publication Date: 2008
  • Doi Number: 10.1080/00397910701739063
  • Title of Journal : SYNTHETIC COMMUNICATIONS
  • Page Numbers: pp.212-216

Abstract

Alkylation of 2-methoxyfuran, followed by in situ TPP-sensitized photooxygenation of 2-methoxy-5-pentylfuran in the presence of Me2S, gave methyl (Z)-4-oxonon-2-enoate. Hydrolysis of methyl (Z)-4-oxonon-2-enoate afforded (E)-4-oxonon-2-enoic acid in three steps and in 79% overall yield.