54233-03-3Relevant academic research and scientific papers
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
Jie, Marcel S. F. Lie Ken,Zheng, Y. F.
, p. 467 - 468 (2007/10/02)
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, 27percent), methyl 5-hexylthiophene-2-octanoate (5, 15percent), and methyl 5-hexylfuran-2-octanoate (6, 9percent).Compound 4 can be conveniently converted to 5 (83percent) by refluxing with trifluoroacetic acid in 1,2-dichloroethane.
