N,N-Dimethylaniline → 16beta-Ethyl-17beta-(2-bromopropionyloxy)-4-estren-3-one

HRID 64705

Reaktionsgleichung

Reaktionsgleichung von HRID 64705
[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[OH:22])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].CN(C)C1C=CC=CC=1.[Br:32][CH:33]([CH3:37])[C:34](Br)=[O:35].C(OCC)(=O)C>ClCCl>[CH2:1]([C@H:3]1[CH2:8][C@H:7]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:5]2([CH3:6])[C@H:4]1[O:22][C:34](=[O:35])[CH:33]([Br:32])[CH3:37])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]

Komponenten

6

Edukt 4

HCID 949N,N-DimethylanilineHCID 8857Ethyl AcetateHCID 79047Propanoyl bromide, 2-bromo-HCID 443947Oxendolone

Produkt 1

HCID 8674097916beta-Ethyl-17beta-(2-bromopropionyloxy)-4-estren-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 70 ml of dichloromethane are dissolved 3.0 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 1.6 ml of N,N-dimethylaniline and, with stirring, 1.2 ml of α-bromopropionyl bromide is added to the above solution. The mixture is stirred at room temperature (15°-25° C.) for 30 hours followed by addition of 300 ml of ethyl acetate. The mixture is washed with 10% sulfuric acid and saturated aqueous sodium chloride solution in that order and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 300 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 600 ml of diisopropyl ether. The eluate is evaporated under reduced pressure to remove the solvent, giving 2.7 g of the above-identified compound as a light-yellow viscous oil.

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature (15°-25° C.) for 30 hours
  2. washThe mixture is washed with 10% sulfuric acid and saturated aqueous sodium chloride solution in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is then distilled off under reduced pressure
  5. washpassage of 300 ml of diisopropyl ether-n-hexane (1:1), elution
  6. customThe eluate is evaporated under reduced pressure
  7. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f6b3b723c1f442e696db14178b654489
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609650

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