18-Crown-6 → Potassium Hydroxide

Participants

Reaction Steps

A solution of 2 parts 4-cholesten-3-one, 2 parts 18-crown-6 and 1.5 parts potassium t-butoxide in 400 parts benzene was stirred for 30 minutes at room temperature under an oxygen atmosphere and worked up in the usual manner. The product, 2-hydroxycholesta-1,4-dien-3-one, was purified by preparative TLC recrystallized from ligroin [M.P. 112.5-113.5] and identified by its spectral data: 1H NMR (CDCl3) δ 6.13 (s,H-4) 6.30 (s,H-1); MS (70 ev)m/e 398 (M+); IR (CHCl3): 3420, 1620, 1605 cm-1. The same enol was obtained when a solution of 1.7 parts of 4-cholesten-3-one, 2.4 parts of 18-crown-6 and 1 part of potassium hydroxide in 350 parts benzene was stirred for 3 days at room temperature under an oxygen atmosphere and worked up in the usual manner. The rate of reaction in this and similar cases can be increased if the oxygen pressure is increased above one atmosphere. :

Provenance & Evidence