一种由氟代炔丙基氯合成炔丙基氟醇和2,5-二取代呋喃的简便新方法。

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

作者信息

Xu Bo, Hammond Gerald B

机构信息

Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.

出版信息

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

DOI:10.1021/jo0601011

PMID:16626134

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.

摘要

氟代炔丙基氯在温和条件下与羰基化合物反应，以良好的产率生成炔丙基氟代醇；然而，在较高温度和较长反应时间下，也能以良好的产率得到2,5-二取代呋喃。氟代醇可用琼斯试剂很容易地氧化为α-氟代酮和α-氟代羧酸。