Water → 3-Chlorocholest-5-en-24-one

HRID 1448021Notes

Reaction equation

HRID 1448021 reaction equation
S(O)(=O)(=O)C.S(O)(=O)(=O)C.O[C@@H:12]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@H:14]([C@@H:15](O)[CH2:16][C@@H:17]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:39])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:30])[CH2:23][CH2:24][C:25](=O)[CH:26]([CH3:28])[CH3:27])[CH2:13]1.[Cl-:41].[Li+].[OH2:43]>CN(C)C=O>[Cl:41][CH:12]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:39])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:30])[CH2:23][CH2:24][C:25](=[O:43])[CH:26]([CH3:27])[CH3:28])[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 86736736HCID 86736736, compound

Product 1

HCID 542306963-Chlorocholest-5-en-24-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 3α,6α-dihydroxy-5β-cholestan-24-one dimesylate prepared (a) above in dimethylformamide (10 ml) was added lithium chloride (100 mg) and the mixture was refluxed for 30 minutes. After cooling, water was added to the reaction mixture and the mixture was extracted with diethyl ether. The ether layer was washed with water, dried over magnesium sulfate and evaporated to give an oily product, 3-chlorocholest-5-en-24-one.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d89eb6be1f574106a180e377f2c12f35
Source dataset
uspto-grants-1979_12
Patent number
US04179452

Reaction notes

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