Water → 24-Ketocholesterol

HRID 1154787Notes

Reaction equation

HRID 1154787 reaction equation
C([O:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=O)C.[OH-].[K+].O>CO.C1C=CC=CC=1>[OH:4][C@H:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:23])[CH2:16][CH2:17][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 1097227324-Oxocholesterol acetate

Product 1

HCID 1103680824-KetocholesterolYield 90%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent2×

Procedure

Specifically, the crude 3β-acetoxy-24-oxocholest-5-ene was dissolved in 100 ml of a mixture of methanol and benzene (1:1). To the solution was added dropwise a 10% methanol solution of potassium hydroxide at room temperature with stirring. After the addition, the mixture was stirred at 70° C. for 4 hours. After the reaction, 100 mg of water was added to separate the reaction mixture into layers. The resulting aqueous layer was extracted twice with benzene. The benzene extracts were combined with the organic layer. The mixture was washed successively with dilute hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated to form 3.6 g (yield: 90% based on 3β-acetoxychol-5-enic acid) of 3β-hydroxy-24-oxocholest-5-ene as a white solid. The properties of the product were as follows:

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 70° C. for 4 hours
  3. additionwas added
  4. customto separate the reaction mixture into layers
  5. extractionThe resulting aqueous layer was extracted twice with benzene
  6. washThe mixture was washed successively with dilute hydrochloric acid
  7. dry with materiala saturated aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8f5633944c1c427b80b50a97033e8f6c
Source dataset
uspto-grants-1981_11
Patent number
US04298537

Reaction notes

Loading…