Download PDF
Synthesis 1988; 1988(6): 467-468
DOI: 10.1055/s-1988-27607
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.