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

HRID 371848Notes

Reaction equation

HRID 371848 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-da5509cdd5ea43fbb119aebf1fc319d8
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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