2-Iodoxybenzoic acid → 5alpha-Cholestan-3-one

Participants

Reaction Steps

A solution of dihydrocholesterol (1.94 g; 5 mmol) in THF (8 ml) was added to a solution of o-iodoxybenzoic acid I (2.10 g, 7.5 mmol) in DMSO (14 ml). After 2 hr precipitation of a white solid was observed. After 5 hr the reaction solution was poured into Na2CO3 (5%, 40 ml) and extracted with diethyl ether/n-hexane (50:50; 3×30 ml). The combined organic layers were washed with water (2×15 ml), dried over sodium sulfate and brought to dryness under vacuum. The residue was crystallised from ethanol to give 1.73 g (89%) of 5α-cholestan-3-one mp 129°-130° C. (lit. 128°-130° C.: Beilsteins Handbuch der organischen Chemie, III E., 7, 1330b).

Provenance & Evidence