Sodium Carbonate → 19-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

HRID 839589

Reaktionsgleichung

Reaktionsgleichung von HRID 839589
[O:1]=[C:2]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:27]([CH2:28][CH2:29][C@:7]12[CH3:8])[C@:20]1([CH2:21][O:22]C(=O)CC)[C:15](=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)[CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:22][CH2:21][C@@:20]12[C@@H:27]3[C@H:12]([C@H:9]4[C@@:7]([CH2:29][CH2:28]3)([CH3:8])[C@@H:6]([O:5][C:2](=[O:1])[CH2:3][CH3:4])[CH2:11][CH2:10]4)[CH2:13][CH2:14][C:15]1=[CH:16][C:17](=[O:30])[CH2:18][CH2:19]2

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 5434261217beta,19-Bis(1-oxopropoxy)-androst-4-en-3-one

Produkt 1

HCID 5422328719-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 11 g of 17β,19-bis(1-oxopropoxy)androst-4-en-3-one in 2 liters of methanol is treated with 2.5 g of sodium carbonate in 250 ml of water and refluxed for one hour after which the reaction mixture is poured into 10 liters of water, and the solid collected by filtration. The solid is dissolved in methylene chloride, dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one. M.P. 160°-162° C.

Aufarbeitung

  1. temperaturerefluxed for one hour after which the reaction mixture
  2. filtrationthe solid collected by filtration
  3. dissolutionThe solid is dissolved in methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue is crystallized from acetone-hexane yielding 6 g of 19-hydroxy-17β(1-oxopropoxy)androst-4-en-3-one

Quellen und Nachweise

ORD-Eintrag
ord-19bcbfb4312144ff922c626cf674453e
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04096254

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