Cholesterol → 1,4,6-Cholestatrien-3-one

HRID 651943

Reaction equation

HRID 651943 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]>O1CCOCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16](=[CH:17][C:18](=[O:19])[CH:20]=[CH:21]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Participants

3

Reactant 1

HCID 5997Cholesterol

Product 1

HCID 1073901,4,6-Cholestatrien-3-oneYield 60.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cholesterol (19.3 gms) and dichlorodicyanoquinone (38 gms) in dry dioxan (500 ml) were heated under reflux for 22 hrs. The mixture was then cooled, filtered and the filtrate evaporated to dryness. Chromatography of the residue on alumina and elution with benzene/hexane followed by elution with benzene afforded the trienone as a pale oil (11.5 gms) which solidified on standing. Physical properties of this material were appropriate.

Workup

  1. temperatureunder reflux for 22 hrs
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. washChromatography of the residue on alumina and elution with benzene/hexane
  6. washfollowed by elution with benzene

Sources & evidence

ORD record
ord-b8b7c550be1944b7b8496543f44a2355
Source dataset
uspto-grants-1987_06
Patent number
US04670190

Linked notes

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