Comparative study on Wittig- Horner reaction and Grignard reaction in synthesis of resveratrol derivative

LIU Qiang;SHENG Wen-bing;LIU Wen-bin;LIN Shi-sang;JI Jie;PENG Cai-yun;Hunan University of Traditional Chinese Medicine;  

Objective: To conduct a comparative study on the synthesis of the resveratrol derivative 3,4,5,4'- tetramethoxystilbene. Methods: The 3,4,5- trimethoxybenzoic acid and anisaldehyde were selected as raw materials and were treated by Na BH4 reduction and SOCl2 halogenation to obtain halogenated hydrocarbons,which were subjected to Wittig- Horner reaction and Grignard reaction to obtain Wittig agent and Grignard agent,respectively. The Wittig agent and Grignard agent were separately mixed with anisaldehyde for condensation to obtain 3,4,5,4'- tetramethoxystilbene. The structure of final product was identified by 1H- nuclear magnetic resonance(1H- NMR) and mass spectrometry( MS). Results:1H- NMR and MS showed that the overall yields of 3,4,5,4'- tetramethoxystilbene synthesized by Wittig- Horner reaction and Grignard reaction were 75. 76% and 15. 96%,respectively,with a significant difference. Conclusion: Compared with Grignard reaction,Wittig- Horner reaction is more favorable for the formation of double bonds in the key steps of preparation of target compound and ensures higher yield and lower cost. Wittig-Horner reaction is more suitable for the complete synthesis of target compound.

【Fund】： 湖南省中医药管理局科研项目(编号:2012163);; 2013年度湖南省大学生创新性实验计划项目(编号:174);; 湖南省药学重点学科资助(编号:2011)
【CateGory Index】： R284.3

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