Potassium Acetate → 3beta-Hydroxycholest-5-en-24-one acetate

HRID 1448022Notes

Reaction equation

HRID 1448022 reaction equation
Cl[CH:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1.[C:30]([O-:33])(=[O:32])[CH3:31].[K+]>C(O)(=O)C>[C:30]([OH:33])(=[O:32])[CH3:31].[OH:32][C@H:2]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:29])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:20])[CH2:13][CH2:14][C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH2:3]1

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 542306963-Chlorocholest-5-en-24-one

Product 1

HCID 867367383beta-Hydroxycholest-5-en-24-one acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To the solution of 3-chlorocholest-5-en-24-one in glacial acetic acid (3 ml) was added anhydrous potassium acetate (0.2 g) and the solution was refluxed for 4 hours. The reaction mixture was concentrated and extracted with diethyl ether. The ether layer was washed with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel to give 81.1 mg of 3β-hydroxycholest-5-en-24-one acetate having a melting point of 125°-127° C. after recrystallization from methanol.

Workup

  1. temperaturethe solution was refluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with diethyl ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-730a62660bc549989b501917ac969219
Source dataset
uspto-grants-1979_12
Patent number
US04179452

Reaction notes

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