A new convenient synthesis of propargylic fluorohydrins and 2,5-disubstituted furans from fluoropropargyl chloride

J Org Chem. 2006 Apr 28;71(9):3518-21. doi: 10.1021/jo0601011.

Abstract

Fluoropropargyl chloride reacted with carbonyl compounds to give propargylic fluorohydrins under mild conditions and in good yields; however, at higher temperatures and longer reaction times, 2,5-disubstituted furans are obtained, also in good yields. Fluorohydrins can be readily oxidized to alpha-fluoroketones and alpha-fluorocarboxylic acids with Jones' reagent.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Furans / chemical synthesis*
  • Hydrocarbons, Cyclic / chemical synthesis*
  • Hydrocarbons, Cyclic / chemistry
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry

Substances

  • Furans
  • Hydrocarbons, Cyclic
  • Hydrocarbons, Fluorinated