Sodium Sulfite → HCID 54306672, compound

HRID 2397995Notes

Reaction equation

HRID 2397995 reaction equation
[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:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][C@H:9]([CH3:22])[C:8]1=[CH:7][C:6](=[O:23])[CH2:5][CH2:4]2.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH3:22][C@@H:9]1[C:8]2[C@:3]([CH:2]=[O:1])([CH2:4][CH2:5][C:6](=[O:23])[CH:7]=2)[C@@H:20]2[C@H:11]([C@H:12]3[C@@:16]([CH2:18][CH2:19]2)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH2:10]1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 7058392519-Hydroxy-6alpha-methyl-4-androstene-3,17-dioneHCID 131709961Jones' reagent

Product 1

HCID 54306672HCID 54306672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 19-hydroxy-6α-methyl-4-androstene-3,17-dione 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 which forms is collected, washed well with water and crystallized from ether-hexane to yield 6α-methyl-4-androstene-3,17,19-trione.

Workup

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

Sources & evidence

ORD record
ord-f48960192fc54a9caaec8d84964d65f4
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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