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Ethyl Acetate → 16beta-Ethyl-17beta-(3-oxobutyryl)oxyacetoxy-4-estren-3-one

HRID 64726
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64726
[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:23](=[O:26])[CH2:24][OH:25])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2].C([O-])(=O)C.[Na+].[CH2:32]=[C:33]1[O:37][C:35](=[O:36])[CH2:34]1.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:23](=[O:26])[CH2:24][O:25][C:35](=[O:36])[CH2:34][C:33](=[O:37])[CH3:32])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 12661DiketeneHCID 517045Sodium AcetateHCID 7046644116beta-Ethyl-17beta-glycoloyloxy-4-estren-3-one

Produkt 1

HCID 7046732716beta-Ethyl-17beta-(3-oxobutyryl)oxyacetoxy-4-estren-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

In 30 ml of dichloromethane is dissolved 0.8 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one, and 0.24 g of anhydrous sodium acetate and 0.3 ml of diketene are added. The mixture is refluxed for 4 hours. After cooling, 100 ml of ethyl acetate is added and the mixture is washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following serial passage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution is carried out with 600 ml of isopropyl ether-ethyl acetate (2:3). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.0 g of the above-identified compound as a light-yellow viscous oil.

Aufarbeitung

  1. additionare added
  2. temperatureThe mixture is refluxed for 4 hours
  3. temperatureAfter cooling
  4. washthe mixture is washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure
  7. washpassage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution
  8. customThe eluate is evaporated under reduced pressure
  9. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-a12a091f133c40afb685201a87e3a710
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04609650

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