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Octanoic Acid → 16beta-Ethyl-17beta-n-octanoyloxyacetoxy-4-estren-3-one

HRID 64713
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64713
[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]Br)[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:27]([OH:36])(=[O:35])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CC(C)=O.[OH-].[Na+].O>[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:36][C:27](=[O:35])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[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 2

HCID 379Octanoic AcidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Produkt 1

HCID 7046698116beta-Ethyl-17beta-n-octanoyloxyacetoxy-4-estren-3-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel
HCID 14798
Sodium Hydroxide
Lösungsmittel

Versuchsvorschrift

In 60 ml of acetone is dissolved 1.0 ml of n-octanoic acid, and 3.0 ml of 2N-NaOH, 15 ml of water and 1.8 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are serially added to the above solution. The mixture is refluxed for 4 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is separated, 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 passage of 50 ml of diisopropyl ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.7 g of the above-identified compound as a colorless oil.

Aufarbeitung

  1. additionare serially added to the above solution
  2. temperatureThe mixture is refluxed for 4 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. extractionthe residue is extracted with 150 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is then distilled off under reduced pressure
  9. washpassage of 50 ml of diisopropyl ether, elution
  10. customThe eluate is evaporated under reduced pressure
  11. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fc929792369a463e95c40cc536834624
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04609650

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