Ammonium Chloride → 1beta-Methyl-5-androstene-3,17-dione

HRID 1733108Notes

Reaction equation

HRID 1733108 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C@H:8]1[C@@:25]2([CH3:26])[C:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:27])=[CH:11][C:10](=[O:28])[CH2:9]1.[Cl-].[NH4+]>CS(C)=O>[CH3:7][C@H:8]1[C@@:25]2([CH3:26])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH2:17][CH2:18][C:19]2=[O:27])[CH2:11][C:10](=[O:28])[CH2:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 541757841beta-Methyl-4-androstene-3,17-dione

Product 1

HCID 705847521beta-Methyl-5-androstene-3,17-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of potassium t-butoxide in dimethylsulfoxide at 25° C. under nitrogen is added 1β-methyl-4-androstene-3,17-dione in dimethylsulfoxide with stirring. After 15 minutes the mixture is poured onto cold aqueous ammonium chloride. The solid is rapidly filtered, washed well with water and dissolved in ether. The ether is washed with water, dried over sodium sulfate and removed at room temperature to yield 1β-methyl-5-androstene-3,17-dione.

Workup

  1. filtrationThe solid is rapidly filtered
  2. washwashed well with water
  3. dissolutiondissolved in ether
  4. washThe ether is washed with water
  5. dry with materialdried over sodium sulfate
  6. customremoved at room temperature

Sources & evidence

ORD record
ord-44224f7a2f13470091e4de825a80be94
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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