Sodium borohydride → 7-[2-Hydroxy-5-(4-ethyl-3-hydroxyoct-1-enyl)-cyclopentyl]heptanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of sodium borohydride (0.095 g.) in 0.2N aqueous sodium hydroxide (0.95 ml.) was added dropwise to a solution of 7-[2-oxo-5-(4-ethyl-3-oxo-1-octenyl)cyclopentyl]heptanoic acid (0.4 g.) in ethanol (9 ml.) and N aqueous sodium hydroxide (1.2 ml.). The resulting solution was stirred for 1 day, and then the ethanol was removed in vacuo. A small quantity of water was added, and the solution was extracted twice with diethyl ether (to remove non-acidic material). The aqueous solution was covered with a layer of diethyl ether and acidified to pH 1 by the dropwise addition of concentrated hydrochloric acid, cooling the solution to about 10°C. The ether layer was separated and the aqueous layer extracted twice more with diethyl ether. The combined ether extracts were dried over magnesium sulphate, evaporated and purified by preparative thin-layer chromatography to give 7[2-hydroxy-5-(4-ethyl-3-hydroxy-1-octenyl)cyclopentyl]heptanoic acid (60 mg.), νmax 1700cm-1, 980 cm- 1. (Found: C, 71.0; H, 10.4. C22H40O4 requires C, 71.7; H, 10.9%).

Provenance & Evidence