Aluminum isopropoxide → 3-Methoxyestra-2,5(10)-dien-17-one

HRID 1077237

Reaktionsgleichung

Reaktionsgleichung von HRID 1077237
[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(=O)CCCCC1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]1=[O:21]

Komponenten

5

Edukt 2

HCID 11143Aluminum isopropoxideHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-ol

Produkt 1

HCID 227914253-Methoxyestra-2,5(10)-dien-17-oneAusbeute 88,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 7967CyclohexanoneLösungsmittel

Versuchsvorschrift

Dissolve dl-3-methoxyestra-2,5(10)-dien-17β-ol (4 g) in cyclohexanone (40 ml) and toluene (140 ml) and add a solution of aluminum isopropoxide (4 g) in toluene (56 ml). Reflux in an atmosphere of nitrogen for two hours and cool. Add water (7.5 ml), shake, and then dry by adding sodium sulfate (10 g). Filter and evaporate under vacuum and recrystallize the residue from methanol to obtain dl-3-methoxyestra-2,5(10)-dien-17-one (3.5 g); m.p. 116°-118°; infrared absorption maxima at 5.76 μ, 5.9 μ, 6.01 μ.

Aufarbeitung

  1. temperatureReflux in an atmosphere of nitrogen for two hours
  2. temperaturecool
  3. dry with materialAdd water (7.5 ml), shake, and then dry
  4. additionby adding sodium sulfate (10 g)
  5. filtrationFilter
  6. customevaporate under vacuum
  7. customrecrystallize the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-b1399acfce7b47e09acec7d0d8711417
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

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