Quinoline → (1R,cis)2,2-dimethyl-3-[Z-2-(pentyloxycarbonyl)ethenyl]-cyclopropane-carboxylic acid

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Reaction Steps

A mixture of 4.8 g of the product of Step B, 50 ml of ethyl acetate, 1 ml of quinoline, 1 g of 10% palladium hydroxide on barium sulfate in 50 ml of ethyl acetate was hydrogenated and the mixture was filtered. The filtrate was washed with N hydrochloric acid, then with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 70-30-1 cyclohexane-ethyl acetate-acetic acid mixture to obtain 3 g of (1R,cis) 2,2-dimethyl-3-[Z-2-(pentyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid.

Provenance & Evidence