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

HRID 1834979Notes

Reaction equation

HRID 1834979 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 under nitrogen at 25° C. is added 1β-methyl-4-androstene-3,17-dione in dimethylsulfoxide with stirring. After 15 minutes the mixture is poured onto a cold aqueous ammonium chloride solution. The solid which forms is rapidly filtered, washed well with water and redissolved in ether. The ether solution is washed with water and dried over sodium sulfate. The ether is removed at room temperature to yield 1β-methyl-5-androstene-3,17-dione.

Workup

  1. filtrationThe solid which forms is rapidly filtered
  2. washwashed well with water
  3. dissolutionredissolved in ether
  4. washThe ether solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe ether is removed at room temperature

Sources & evidence

ORD record
ord-9027c8b3a8ee4b6cb3e635ab88557139
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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