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

HRID 2397975Notes

Reaction equation

HRID 2397975 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2fa7a460882c4a3f94cde76f0db349b7
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

Loading…