Androsta-1,4-diene-3,17-dione → 1,5-Androstadiene-3,17-dione

HRID 1733103Notes

Reaction equation

HRID 1733103 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C@:8]12[CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH2:15][C:16]4[C@:21]3([CH3:22])[CH:20]=[CH:19][C:18](=[O:26])[CH:17]=4)[C@@H:12]1[CH2:11][CH2:10][C:9]2=[O:27].[Cl-].[NH4+]>CS(C)=O>[CH3:7][C@:8]12[CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH:15]=[C:16]4[C@:21]3([CH3:22])[CH:20]=[CH:19][C:18](=[O:26])[CH2:17]4)[C@@H:12]1[CH2:11][CH2:10][C:9]2=[O:27]

Participants

5

Reactant 3

HCID 13472Androsta-1,4-diene-3,17-dioneHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 572670321,5-Androstadiene-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 1,4-androstadiene-3,17-dione in dimethylsulfoxide with stirring. After fifteen 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 solution is washed again with water, dried over sodium sulfate and evaporated at room temperature to yield 1,5-androstadiene-3,17-dione.

Workup

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

Sources & evidence

ORD record
ord-af4ec14581884154bc4bd27ac3379935
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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