18-Crown-6 → Potassium Hydroxide

HRID 354666Notes

Reaction equation

HRID 354666 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[CH2:29]1[O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30]1.CC(C)([O-:50])C.[K+:52]>C1C=CC=CC=1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1].[CH2:32]1[O:31][CH2:30][CH2:29][O:46][CH2:45][CH2:44][O:43][CH2:42][CH2:41][O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33]1.[OH-:50].[K+:52]

Participants

7

Reactant 3

HCID 2855718-Crown-6HCID 91477Cholest-4-en-3-oneHCID 23665647Potassium tert-butoxide

Product 3

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 91477Cholest-4-en-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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. :

Workup

  1. customThe product, 2-hydroxycholesta-1,4-dien-3-one, was purified by preparative TLC
  2. customrecrystallized from ligroin [M.P. 112.5-113.5]

Sources & evidence

ORD record
ord-3397bff08c5943ec8d67e0c433e72e00
Source dataset
uspto-grants-1983_03
Patent number
US04376733

Reaction notes

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