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Efficient Synthesis of Long-Chain Furanoid Fatty Ester Derivative From Methyl Ricinoleate

 

作者: M.S.F.Lie Ken Jie,   M.S. K. Syed-rahmatullah,   K.P. Wong,  

 

期刊: Natural Product Letters  （Taylor Available online 1992）
卷期: Volume 1, issue 2  

页码: 93-98

 

ISSN:1057-5634

 

年代: 1992

 

DOI:10.1080/10575639208048894

 

出版商: Taylor & Francis Group

 

关键词: ammonium azide;Lewis acid;tin(II) halide;epoxy-oxo fatty ester;furanoid fatty ester;synthesis

 

数据来源: Taylor

 

摘要:

The reaction of methyl (Z)-9,10-epoxy-12-oxoocta-decanoate (2) with ammonium azide, generatedin situfrom sodium azide and ammonium chloride in aqueous ethanol affords methyl 8-(5-hexylfuran-2-yl)octanoate (1b) in 98% yield. Compound1bwas also prepared in >90% yield by reacting compound 2 with the following Lewis acids: aluminium(III) chloride, tin(IV) chloride, zinc(II) chloride under reflux in benzene or dichloromethane; or at ambient temperature with tin(II) bromide or hydrated tin(II) chloride in dichloroethane.

 

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