Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1965-1969.DOI: 10.6023/cjoc201205005 Previous Articles     Next Articles

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2-乙酰氧甲基吡咯衍生物和醇钠的醚化反应研究

严兆华, 余章昕, 刘永杰, 胡伟   

  1. 南昌大学理学院化学系 南昌 330031
  • 收稿日期:2012-05-05 修回日期:2012-06-07 发布日期:2012-06-21
  • 通讯作者: 严兆华 E-mail:yanzh@ncu.edu.cn
  • 基金资助:

    江西省自然科学基金(No. 2009GZH0078)资助项目.

Etherification of 2-Acetoxymethylpyrrole Derivative with Sodium Alkoxide

Yan Zhaohua, Yu Zhangxin, Liu Yongjie, Hu Wei   

  1. Department of Chemistry, Nanchang University, Nanchang 330031
  • Received:2012-05-05 Revised:2012-06-07 Published:2012-06-21
  • Supported by:

    Project supported by the Natural Science Foundation of Jiangxi Province (No. 2009GZH0078).

Etherification of 2-acetoxymethylpyrrole derivative with sodium alkoxide at reflux was investigated in details resulting in the smooth formation of the corresponding 2-alkoxymethylpyrrole derivative in excellent yield. A plausible mechanism involving the formation of a highly reactive intermediate azafulvene species was proposed to explain the observed transformation. An alternate method for the preparation of 2-alkoxymethylpyrrole derivative starting from 2-acetoxymethylpyrrole derivative in alkaline media was provided.

Key words: 2-acetoxymethylpyrrole derivative, 2-alkoxymethylpyrrole derivative, etherification, azafulvene, sodium alkoxide