Chemical Research in Chinese Universities ›› 2010, Vol. 26 ›› Issue (1): 55-59.

• Articles • Previous Articles     Next Articles

Practical and Efficient Acylation and Tosylation of Sterically Hindered Alcohols Catalyzed with 1-Methylimidazole

WU Qin-pei1*, LIU Hua2, LIU Hai-xia1, CHEN Xi1, WANG Hao2, ZHANG Qing-shan1 and LI Yun-zheng1   

  1. 1. Department of Applied Chemistry,
    2. School of Life Science, Beijing Institute of Technology, Beijing 100081, P. R. China
  • Received:2009-01-15 Revised:2009-04-09 Online:2010-01-04 Published:2010-03-29
  • Contact: WU Qin-pei. E-mail: qpwu@bit.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.30340070).

Abstract:

Acylation of sterically hindered alcohols is frequently encountered in synthetic chemistry. An efficient and mild procedure for tosylation and esterification of sterically hindered hydroxyl groups with p-TsCl, Ac2O and Bz2O in the presence of 1-methylimidazole is described. It was observed that auxiliary base, triethylamine, accelerates the acylation reaction.

Key words: Esterification; Imidazole; Nucleophilic catalysis; Organocatalysis