Acetic Acid → 6-(5-Cholesten-3beta-yloxy)hex-3-yne-1-ol

Participants

Reaction Steps

A suspension of 6-(5-cholesten-3β-yloxy)-1-(triphenylmethyloxy)hex-3-yne (21 g) in p-dioxan (40 ml) is heated on a steam cone until dissolution. This is followed by the addition of 90% acetic acid (30 ml) until turbidity, and the reaction mixture is heated overnight at 100°. Water (15 ml) is added and the mixture is concentrated to a small volume. Ether and petroleum ether are added and crystals (triphenylmethanol) are filtered and discarded. The filtrate is concentrated to dryness and put on a silica gel column and eluted with 20% ether in petroleum ether. The desired compound, 6-(5-cholesten-3β-yloxy)hex-3-yne-1-ol, is isolated as an oil (7.0 g).

Provenance & Evidence