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

HRID 1834918Notes

Reaction equation

HRID 1834918 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-d0716156564048e8a7dcea7b5e4636b4
Source dataset
uspto-grants-1978_01
Patent number
US04071624

Reaction notes

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