Sodium Sulfite → 1alpha-Methyl-4-androstene-17,19-dione

HRID 1834918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1834918
[CH3:1][C@@H:2]1[C@@:19]2([CH2:20][OH:21])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:22])=[CH:5][CH2:4][CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH3:1][C@@H:2]1[C@@:19]2([CH:20]=[O:21])[C:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:22])=[CH:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 705847581alpha-Methyl-4-androstene-17beta,19-diolHCID 131709961Jones' reagent

Produkt 1

HCID 537816751alpha-Methyl-4-androstene-17,19-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1α-Methyl-4-androstene-17β,19-diol is dissolved in dimethylformamide at 40° C. and two equivalents of Jones Reagent are added all at once. The mixture is stirred for about 5 hours at 40° C., cooled and a 1% aqueous sodium sulfite solution is added. After several hours the crystals which form are collected by filtration, thoroughly washed with water and air dried. Crystallization from hexane yields the desired 1α-methyl-4-androstene-17,19-dione.

Aufarbeitung

  1. temperaturecooled
  2. filtrationAfter several hours the crystals which form are collected by filtration
  3. washthoroughly washed with water and air
  4. customdried
  5. customCrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-d0716156564048e8a7dcea7b5e4636b4
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04071624

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