Methanol → Cholest-5-ene-1alpha,3beta-diol

HRID 444411Notes

Reaction equation

HRID 444411 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C@H:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22](=[CH:23][C@@H:24]([OH:35])[CH2:25][C@@H:26]2[OH:34])[CH:21]=[CH:20]3)[CH2:17][CH2:16]1)[CH3:14])[CH3:9].CO>CCOCC>[OH:34][C@@H:26]1[C@@:27]2([CH3:28])[C:22](=[CH:21][CH2:20][C@@H:19]3[C@@H:29]2[CH2:30][CH2:31][C@@:32]2([CH3:33])[C@H:18]3[CH2:17][CH2:16][C@@H:15]2[C@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:8]([CH3:9])[CH3:7])[CH2:23][C@@H:24]([OH:35])[CH2:25]1

Participants

5

Reactant 3

HCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 228157444,6-Cholestandien-1alpha,3beta-diol

Product 1

HCID 11112200Cholest-5-ene-1alpha,3beta-diolYield 72%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1α-hydroxycholesteryl tosylate (7, R' is 4-methylphenyl, 1.35 g) in anhydrous ether (80 ml) was heated under reflux with lithium aluminum hydride (0.098 g, 23.9 mmoles) under anhydrous conditions for 5 hours. Work-up of the reaction mixture as described in the above procedure for the preparation of 4,6-cholestadien-1α,3β-diol 4 followed by chromategraphy of the crude carbinol on silica gel (25 g) using low boiling petroleum ether-benzene as the eluent gave 705 mg (72% yield based on 1α-hydroxycholesterol 6) of 5.

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-b5fb8c05a4d54ae0808ebefd549a1bd7
Source dataset
uspto-grants-1981_04
Patent number
US04264512

Reaction notes

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