Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1915-1920.DOI: 10.6023/cjoc201601040 Previous Articles     Next Articles



康海霞a, 白静b, 郗振涛a, 张曼曼a, 傅玉琴a, 邹大鹏b   

  1. a 洛阳师范学院化学化工学院 洛阳 471022;
    b 郑州大学化学与分子工程学院 郑州 450001
  • 收稿日期:2016-01-29 修回日期:2016-03-22 发布日期:2016-05-03
  • 通讯作者: 傅玉琴
  • 基金资助:

    河南省科技发展计划(No. 122300410265)及洛阳师范学院2013年培育基金(No. 2013-PYJJ-006)资助项目.

Reaction of 5(R)-(l-Menthoxy)-2(5H)-furanone with Diethyl Bromomalonate

Kang Haixiaa, Bai Jingb, Xi Zhentaoa, Zhang Manmana, Fu Yuqina, Zou Dapengb   

  1. a College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
  • Received:2016-01-29 Revised:2016-03-22 Published:2016-05-03
  • Supported by:

    Project supported by the Foundation of Science and Technology of Henan Province (No.122300410265) and the Fostering Foundation of Luoyang Normal University in 2013 (No. 2013-PYJJ-006).

The reaction of 5(R)-(l-menthoxy)-2(5H)-furanone and diethyl bromomalonate was investigated in the presence of anhydrous K2CO3 and phase transfer catalyst tetrabutylammonium bromide (TBAB) using CH3CN as solvent at 80 ℃. In the above condition, the expected novel chiral cyclopropane/butyrolactone derivative 3 with two ethyl ester groups was obtained, and at the same time, another chiral cycloproane/butyrolactone 5 bearing only one ethyl ester group, and trace amount of bromo-substitued compound 6 were also obtained. The possible mechanism was proposed based on the analysis of the products.

Key words: 2(5H)-furanone, cyclopropane/butyrolactone derivative, chiral, synthesis, crystal structure