Yasuo Nakada, Rokuro Endo, Shigeki Muramatsu
1979
Citations
0
Influential Citations
10
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A new method is described for the stereoselective synthesis of trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid (2t) via ethyl 3,3-dimethyl-4,6,6,6-tetrachlorohexanoate (3a) as a key intermediate. The key intermediate (3a) was obtained by addition of carbon tetrachloride to ethyl 3,3-dimethyl-4-pentenoate, prepared by condensation of 3-methyl-2-buten-1-ol and triethyl orthoacetate followed by Claisen rearrangement. Treatment of 3a with sodium t-pentyloxide in benzene gave ethyl trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)-1-cyclopropanecarboxylate (6t) in good yield. Dehydrochlorination and hydrolysis of 6t using potassium hydroxide in ethanol afforded 2t in high yield.