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

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.