Dichloromethane → 69853-71-0

HRID 726528Notes

Reaction equation

HRID 726528 reaction equation
ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:15][C@@H:16]([C@@H:23]1[C@@:27]2([CH3:43])[CH2:28][CH2:29][C@@H:30]3[C@@:35]4([CH3:41])[CH2:36][CH2:37][C@H:38]([OH:40])[CH2:39][C:34]54[O:42][CH:33]5[CH2:32][C@H:31]3[C@@H:26]2[CH2:25][CH2:24]1)[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]>CCOCC>[OH:42][CH:33]1[C:34]2[C@:35]([CH3:41])([CH2:36][CH2:37][C:38](=[O:40])[CH:39]=2)[C@@H:30]2[C@H:31]([C@H:26]3[C@:27]([CH3:43])([CH2:28][CH2:29]2)[C@@H:23]([C@H:16]([CH3:15])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:24][CH2:25]3)[CH2:32]1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 6453234Cholestan-3-ol, 5,6-epoxy-, (3b)-HCID 178418287HCID 178418287, compound

Product 1

HCID 305339969853-71-0Yield 51.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dichloromethane (50 ml) was added to pyridinium chlorochromate (2.78 g, 12.9 mmol) and molecular shieves (3 A) (4.37 g) and the mixture was stirred under a nitrogen atmosphere at room temperature for 15 minutes. To the resulting mixture was added a dichloromethane solution (30 ml) of 5,6-epoxycholesterol (α:β=5:1) (3.323 g, 8.6 mmol) prepared by the method of Fieser and Fieser (L. F. Fieser and H. Fieser, Reagents for Organic Synthesis, Vol. 1: 136, 1967) and the mixture was stirred for 3 hours. Ether (300 ml) was added to the reaction solution and the resulting solution was filtered through silica gel-magnesium sulfate. The organic layer was washed twice with 50 ml of a saturated saline solution and dried. The solvents were distilled off and the residue was purified by column chromatography. 6-Hydroxy-4-cholesten-3-one (α:β=5:1) was obtained as a colorless crystal from the hexane-ethyl acetate (5:1) eluate (yield: 51.7%).

Workup

  1. customprepared by the method of Fieser and Fieser (L. F. Fieser and H. Fieser, Reagents for Organic Synthesis, Vol. 1: 136, 1967)
  2. stirringthe mixture was stirred for 3 hours
  3. filtrationthe resulting solution was filtered through silica gel-magnesium sulfate
  4. washThe organic layer was washed twice with 50 ml of a saturated saline solution
  5. customdried
  6. distillationThe solvents were distilled off
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8b16f032edba4b58a420620507372e2d
Source dataset
uspto-grants-1998_01
Patent number
US05710143

Reaction notes

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