Synthesis 1988; 1988(6): 467-468
DOI: 10.1055/s-1988-27607
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A Convenient Route to a Linear C18 Carboxylic Acid Derivative Containing a Thiophene Ring in the Chain via a 9,10-Epithio-12-oxo Intermediate

Marcel S. F. Lie Ken Jie* , Y. F. Zheng
  • *Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong
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Publication History

Publication Date:
20 August 2002 (online)

Methyl ricinoleate (1) is oxidized to methyl 12-oxo-cis-9-octadecenoate (2) with chromic acid; epoxidation then affords methyl cis-9, 10-epoxy-12-oxooctadecanoate (3). Treatment of 3 with dimethylthioformamide in presence of trifluoroacetic acid gives a mixture of methyl cis-9,10-epithio-12-oxooctadecanoate (4, 27%), methyl 5-hexylthiophene-2-octanoate (5, 15%), and methyl 5 -hexylfuran-2-octanoate (6, 9%) Compound 4 can be conveniently converted to 5 (83%) by refluxing with trifluoroacetic acid in 1,2-dichloroethane.