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

HRID 651943

Reaktionsgleichung

Reaktionsgleichung von HRID 651943
[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]

Komponenten

3

Edukt 1

HCID 5997Cholesterol

Produkt 1

HCID 1073901,4,6-Cholestatrien-3-oneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b8b7c550be1944b7b8496543f44a2355
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670190

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