Citation: Kang Haixia, Bai Jing, Xi Zhentao, Zhang Manman, Fu Yuqin, Zou Dapeng. Reaction of 5(R)-(l-Menthoxy)-2(5H)-furanone with Diethyl Bromomalonate[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1915-1920. doi: 10.6023/cjoc201601040 shu

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

Kang Haixia ^a ,
Bai Jing ^b ,
Xi Zhentao ^a ,
Zhang Manman ^a ,
Fu Yuqin ^a,*,, ,
Zou Dapeng ^b

a.
College of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022
b.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Fu Yuqin, lyfuyuqin@126.com
Received Date: 29 January 2016
Revised Date: 22 March 2016

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

Figures(7)

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