Dimethylformamide → 16beta-Ethyl-17beta-cyclohexylacetoxyacetoxy-4-estren-3-one

HRID 64728

Reaktionsgleichung

Reaktionsgleichung von HRID 64728
[CH:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH2:13]([C@H:15]1[CH2:20][C@H:19]2[C@H:21]3[C@H:30]([CH2:31][CH2:32][C@:17]2([CH3:18])[C@H:16]1[O:34][C:35](=[O:38])[CH2:36]Br)[C@@H:29]1[C:24](=[CH:25][C:26](=[O:33])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3)[CH3:14].CN(C=O)C>CC(C)=O.C(OCC)(=O)C.O>[CH2:13]([C@H:15]1[CH2:20][C@H:19]2[C@H:21]3[C@H:30]([CH2:31][CH2:32][C@:17]2([CH3:18])[C@H:16]1[O:34][C:35](=[O:38])[CH2:36][O:9][C:8](=[O:10])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@@H:29]1[C:24](=[CH:25][C:26](=[O:33])[CH2:27][CH2:28]1)[CH2:23][CH2:22]3)[CH3:14]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 21363Cyclohexaneacetic acidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

Produkt 1

HCID 7046711416beta-Ethyl-17beta-cyclohexylacetoxyacetoxy-4-estren-3-oneAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 20 ml of acetone is dissolved 0.65 g of cyclohexylacetic acid, and 2.5 ml of 2N-NaOH, 1.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF are serially added to the above solution. The mixture is refluxed for 5 hours. After cooling, the reaction mixture is poured into a mixture of 100 ml of water and 150 ml of ethyl acetate. The ethyl acetate layer is separated and the aqueous layer is extracted with 100 ml of ethyl acetate. These organic layers are combined, 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 silica gel column chromatography. Following passage of 200 ml of n-hexane-diisopropyl ether (6:4), elution is carried out with 600 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.1 g of the above-identified compound as a light-yellow viscous oil.

Aufarbeitung

  1. additionare serially added to the above solution
  2. temperatureThe mixture is refluxed for 5 hours
  3. temperatureAfter cooling
  4. customThe ethyl acetate layer is separated
  5. extractionthe aqueous layer is extracted with 100 ml of ethyl acetate
  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 200 ml of n-hexane-diisopropyl ether (6:4), elution
  10. additionis carried out with 600 ml of a 1:1 mixture of the same solvents
  11. customThe eluate is evaporated under reduced pressure
  12. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-8d52ce1e572246c59713121a0e934557
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609650

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