Isopropenyl acetate → Cholesta-1,5,7-trien-3-ol

HRID 3987

Reaktionsgleichung

Reaktionsgleichung von HRID 3987
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH:19]=[CH:20]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[K].C(OC(C)=C)(=O)C>C(OCCCC)(=O)C>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][CH:18]([OH:28])[CH:19]=[CH:20]2)=[CH:15][CH:14]=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

Komponenten

5

Edukt 3

HCID 7916Isopropenyl acetateHCID 1073901,4,6-Cholestatrien-3-oneHCID 5462222Potassium

Produkt 1

HCID 18611553Cholesta-1,5,7-trien-3-olAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31272Butyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 19 g (0.05 mol) of cholesta-1,4,6-trien-3-one (I), 6.8 g (0.05 mol) of potassium acid sulphate and 200 g (2 mol) of isopropenyl acetate were added 200 ml of butyl acetate, and the resulting mixture was heated under reflux for 7 hours. After completion of the reaction, the same treatment as in Example 1 was carried out to yield 11.1 g of cholesta-1,5,7-trien-3-ol (IV). The yield was 58%.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 7 hours
  3. customAfter completion of the reaction

Quellen und Nachweise

ORD-Eintrag
ord-8fa7272f95be4725909831043f7554af
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723045

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