Hydrochloric Acid → (E)-8-[3-(3-thienyl)phenyl]-3-oxo-7-octenoic acid methyl ester

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Reaction Steps

3.64 g of the above nitrile compound and 3.92 g of activated zinc powder are added to 50 ml of tetrahydrofuran, 4.54 ml of bromoacetic acid methyl ester is added dropwise to this mixture over a period of 1 hour under reflux with heating and stirring, and the mixture is further stirred under reflux for 1 hour. 100 ml of 10% hydrochloric acid is added to the reaction solution, the mixture is stirred at room temperature for 30 minutes, tetrahydrofuran is distilled off under reduced pressure, and methylene chloride is added to the residual solution for extraction. The extract is washed with saturated saline and post-treated in a conventional manner, and the product is purified by silica gel column chromatography [Wako gel C-200, 100 g; hexane/ethyl acetate=4/1] to obtain 2.33 g of (E)-8-[3-(3-thienyl)phenyl]-3-oxo-7-octenoic acid methyl ester as colorless oil.

Provenance & Evidence