Sodium borohydride → 7-[2-Hydroxy-5-(3-hydroxy-1-octyl)cyclopentyl]heptanoic acid

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Reaction Steps

A solution of the crude 7-[2-oxo-5-(3-oxo-1-octyl)cyclopentyl]heptanoic acid (0.8 g.) in ethanol (20 ml.) was neutralised by addition of 1N sodium hydroxide (2.40 ml.). The resulting solution was then treated with a solution of sodium borohydride (0.25g.) in 0.2 N sodium hydroxide (2.5 ml.) and stirred at ambient temperature for 1 day. The ethanol was then evaporated in vacuo, water added and any non-acidic material removed by extraction with diethyl ether. The aqueous phase was covered with a layer of diethyl ether and acidified by dropwise addition of hydrochloric acid. The ether layer was separated and the aqueous phase extracted again with diethyl ether. The combined ether extracts were dried over sodium sulphate and evaporated to give 7-[2-hydroxy-5-(3-hydroxy-1-octyl)cyclopentyl]heptanoic acid (0.6 g.).

Provenance & Evidence