Water → 3-Oxo-17beta(1oxopropoxy)androst-4en-19-al

HRID 1678957

Reaktionsgleichung

Reaktionsgleichung von HRID 1678957
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C@@H:15]([O:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:26])[CH2:5][CH2:4]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[O:26]=[C:6]1[CH2:5][CH2:4][C@@:3]2([CH:2]=[O:1])[C:8]([CH2:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[O:21][C:22](=[O:25])[CH2:23][CH3:24])=[CH:7]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5422328719-Hydroxy-17beta(1-oxopropoxy)androst-4-en-3-oneHCID 131709961Jones' reagent

Produkt 1

HCID 867345753-Oxo-17beta(1oxopropoxy)androst-4en-19-al

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 14 g of 19-hydroxy-17β-(1-oxopropoxy)androst-4-en-3-one in 1 liter of acetone cooled in an ice bath is added 13.3. ml of Jones reagent over 1 hour after which the reaction mixture is poured into a large volume of water and extracted with ether. The ether extract is dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane to give 3-oxo-17β(1-oxopropoxy)-androst-4-en-19-al, M.P. 119°-121° C.

Aufarbeitung

  1. additionis added 13.3
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialis dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed
  7. customThe residue is crystallized from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-2dc0fb2caf424bf7a781d1ba9d0a4003
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04078060

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