Water → 1-(1-Methoxycarbonylvinyl)cyclopropanecarboxylic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-trifluoromethanesulfonyloxyvinyl)cyclopropane carboxylic acid methyl ester (4.36 g) prepared in the previous step in N,N-dimethylformamide/methanol (1/2, 66 ml) were sequentially added triethylamine (6.4 ml) and bis(triphenylphosphine)palladium (II) dichloride (1.07 g) at room temperature, and the air in reaction vessel was replaced with carbon monooxide at normal pressure. This reaction solution was stirred at 50° C. for 18 hours, and then cooled to room temperature, and carbon monooxide in the reaction vessel was replaced with nitrogen. To this reaction mixture were added water and ethyl acetate, the mixture was filtered through Celite, and subjected to elution with ethyl acetate. The filtrate was extracted with ethyl acetate, the separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/1) to give the titled compound (720 mg).

Provenance & Evidence