27409-41-2 → 3-Oxocholestane

HRID 267245Notes

Reaction equation

HRID 267245 reaction equation
[OH:1][CH:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:3]1>[Si]([O-])([O-])([O-])[O-].[Ag+].[Ag+].[Ag+].[Ag+].C(OCC)(=O)C>[CH3:18][CH:16]([CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:11]1[C@:20]2([CH3:28])[C@H:8]([C@H:7]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:27])[CH:4]([CH2:3][C:2](=[O:1])[CH2:26][CH2:25]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:19])[CH3:17]

Participants

4

Reactant 1

HCID 1099274827409-41-2

Product 1

HCID 108835733-Oxocholestane

Reagents, catalysts & solvents 2

HCID 86733097HCID 86733097, compoundCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

388.6 Mg of 3-hydroxy-cholestane, 500 mg of silver silicate and 30 ml of ethyl acetate were added to the flask of Example II and the reaction mixture was refluxed for 10 hours. Another 50 mg of silver silicate were added thereto and reflux was continued for 5 hours. The mixture was then filtered and the filtrate was concentrated to dryness. The residue was dissolved in ether and the ether was distilled off under reduced pressure to obtain 383 mg of cholestane-3-one melting at 115°C, then 128°C.

Workup

  1. temperaturethe reaction mixture was refluxed for 10 hours
  2. temperaturereflux
  3. filtrationThe mixture was then filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in ether
  6. distillationthe ether was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4fbb10febead4223a6e2c96361c6023a
Source dataset
uspto-grants-1976_03
Patent number
US03941811

Reaction notes

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