Cyclohexanone → Methoxygonadiene

HRID 1414994

Reaktionsgleichung

Reaktionsgleichung von HRID 1414994
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].C1(=O)CCCCC1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O.C1(C)C=CC=CC=1>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20][CH3:21])[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])[CH3:2]

Komponenten

7

Edukt 4

HCID 7967CyclohexanoneHCID 11143Aluminum isopropoxideHCID 24436Sodium SulfateHCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

Produkt 1

HCID 102242Methoxygonadiene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Reflux a mixture of 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.8 g.), aluminium isopropoxide (0.36 g.), toluene (26 cc.) and cyclohexanone (8 cc.) under nitrogen for 3 hours. Allow the solution to cool under nitrogen, add water (5 cc.) and shake the mixture vigorously. Add anhydrous sodium sulphate (5 g.), shake the mixture again, and then allow to stand for 30 minutes. Filter the solution, combine the filtrate with ether-washings of the residue, and evaporate, first at 30°/20 mm., then at 50°/0.1 mm. to leave as a crystalline solid 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one; infrared absorption peaks at 5.78, 5.92, 6.01 μ, with no absorption due to hydroxyl.

Aufarbeitung

  1. temperatureReflux
  2. temperatureAllow the solution to cool under nitrogen
  3. filtrationFilter the solution
  4. customevaporate, first at 30°/20 mm
  5. customat 50°

Quellen und Nachweise

ORD-Eintrag
ord-d73e043756bc41bfa10a4cdffd715bb4
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04002746

Verknüpfte Notizen

Wird geladen…