Methanesulfonic Acid → Cholesta-1,5,7-trien-3-ol

HRID 3986

Reaktionsgleichung

Reaktionsgleichung von HRID 3986
[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].CS(O)(=O)=O.C(OC(C)=C)(=O)C>C1(C)C=CC=CC=1>[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 6395Methanesulfonic AcidHCID 7916Isopropenyl acetateHCID 1073901,4,6-Cholestatrien-3-one

Produkt 1

HCID 18611553Cholesta-1,5,7-trien-3-olAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 19 g (0.05 mol) of cholesta-1,4,6-trien-3-one (I), 4.8 g (0.05 mol) of methanesulfonic acid and 200 g (2 mol) of isopropenyl acetate were added 200 ml of toluene, and the resulting mixture was then heated under reflux for 6 hours. After completion of the reaction, the same treatment as in Example 1 was carried out to yield 11.7 g of cholesta-1,5,7-trien-3-ol (IV). The yield was 61%.

Aufarbeitung

  1. temperaturethe resulting mixture was then heated
  2. temperatureunder reflux for 6 hours
  3. customAfter completion of the reaction

Quellen und Nachweise

ORD-Eintrag
ord-d91476894bba4ff4b3f1ab9b2aac825a
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723045

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