25-Hydroxycholesterol → 25-Hydroxycholesta-1,4,6-trien-3-one

HRID 651947

Reaktionsgleichung

Reaktionsgleichung von HRID 651947
[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:4])[CH3:3]>O1CCOCC1>[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17](=[CH:18][C:19](=[O:20])[CH:21]=[CH:22]2)[CH:16]=[CH:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:3])[CH3:4]

Komponenten

3

Edukt 1

HCID 6509425-Hydroxycholesterol

Produkt 1

HCID 2279738725-Hydroxycholesta-1,4,6-trien-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

25-Hydroxycholesterol (3.4 gms) and dichlorodicyanoquinone (6.5 gms) dissolved in purified dioxan (100 mls) were heated at reflux for 20 hrs. The mixture was filtered and the solvent evaporated. Chromatography of the residue on alumina and elution with ethyl acetate and benzene afforded the trienone. Recrystallization from methanol gave the title compound, melting point 183°-184°. νmax. 3600, 1650 and 1600 cm-1.

Aufarbeitung

  1. temperaturewere heated
  2. temperatureat reflux for 20 hrs
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated
  5. washChromatography of the residue on alumina and elution with ethyl acetate and benzene
  6. customafforded the trienone
  7. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-3c2068ef9cc742e1ade3feaa90bafb20
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670190

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