Methyl chloroformate → HCID 17930266, compound

Participants

Reaction Steps

A solution of 220 mg (1.3 mmol) of 1-(7-carboxyheptyl)-cyclopropene in ether was cooled to 0° C. Triethylamine (0.20 g, 2 mmol) was added, then 0.12 g (1.3 mmol) of methylchloroformate was added. After 2 hours at 0° C., the reaction mixture was transferred to a separatory funnel. The ether phase was washed with water (2×) and brine, dried over magnesium sulfate, filtered and stripped. The product was dissolved in ethanol, cooled in an ice bath and treated with 1 ml of a 21% sodium ethoxide in ethanol solution. The reaction mixture was stirred ½ hour, then water and ether were added. The ether phase was washed with 1N sodium hydroxide solution, water, and brine, dried over magnesium sulfate, filtered and stripped to give 10 mg of 75% pure 7-cycloprop-1-enyl-heptanoic acid ethyl ester.

Provenance & Evidence