Sodium Sulfite → 17beta-Hydroxy-1alpha-methyl-4-androsten-19-one propionate

HRID 2397977Notes

Reaction equation

HRID 2397977 reaction equation
[C:1]([O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:23]([CH2:24][CH2:25][C@:7]12[CH3:8])[C@:20]1([CH2:21][OH:22])[C:15](=[CH:16][CH2:17][CH2:18][C@@H:19]1[CH3:26])[CH2:14][CH2:13]3)(=[O:4])[CH2:2][CH3:3].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].[OH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:23]([CH2:24][CH2:25][C@:7]12[CH3:8])[C@:20]1([CH:21]=[O:22])[C:15](=[CH:16][CH2:17][CH2:18][C@@H:19]1[CH3:26])[CH2:14][CH2:13]3

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 705847651alpha-Methyl-4-androstene-17beta,19-diol 17-propionateHCID 131709961Jones' reagent

Product 1

HCID 8673473517beta-Hydroxy-1alpha-methyl-4-androsten-19-one propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1α-methyl-4-androstene-17β,19-diol 17-propionate in dimethylformamide at 40° C. is rapidly added one equivalent of Jones Reagent. The solution is stirred for about 5 hours at 40° C., cooled and a 1% aqueous sodium sulfite solution is added. The precipitate is collected, washed well with water and crystallized from hexane to yield 17β-hydroxy-1α-methyl-4-androsten-19-one propionate.

Workup

  1. customat 40° C.
  2. temperaturecooled
  3. customThe precipitate is collected
  4. washwashed well with water
  5. customcrystallized from hexane

Sources & evidence

ORD record
ord-c390a286b1c043d581cfd50232141393
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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