5,6-Epoxycholest-7-en-3-ol → HCID 57311702, compound

HRID 1019017Notes

Reaction equation

HRID 1019017 reaction equation
[O:1]1[C@@H:3]2[CH:4]=[C:5]3[C@@H:21]([C@@:22]4([CH3:28])[CH2:23][CH2:24][C@H:25]([OH:27])[CH2:26][C@@:2]124)[CH2:20][CH2:19][C@@:18]1([CH3:29])[C@H:6]3[CH2:7][CH2:8][C@@H:9]1[C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15]>[K]>[CH3:16][CH:14]([CH2:13][CH2:12][CH2:11][C@H:10]([C@@H:9]1[C@:18]2([CH3:29])[C@H:6]([C:5]3[C@H:21]([CH2:20][CH2:19]2)[C@:22]2([CH3:28])[C@@:2]([OH:1])([CH2:26][C@@H:25]([OH:27])[CH2:24][CH2:23]2)[CH2:3][CH:4]=3)[CH2:7][CH2:8]1)[CH3:17])[CH3:15]

Participants

3

Reactant 1

HCID 1258595,6-Epoxycholest-7-en-3-ol

Product 1

HCID 57311702HCID 57311702, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 5462222PotassiumSolvent

Procedure

5,6βEpoxy-5β-cholest-7-en-3β-ol [J. Org. Chem. 50(1985), 1835] (150 mg) is dissolved in 2.5 ml of a potassium hydroxyde solution (5% in methanol). The reaction mixture is refluxed for one hour. Aqueous work-up, extraction with ethylacetate and column chromatography yields 5βcholest-7-ene-3β,5β-diol (54 mg).

Workup

  1. temperatureThe reaction mixture is refluxed for one hour
  2. extractionAqueous work-up, extraction with ethylacetate and column chromatography

Sources & evidence

ORD record
ord-bb59a06640cb44cab4a1d66db71ac0c1
Source dataset
uspto-grants-2002_11
Patent number
US06486145B2

Reaction notes

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