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

HRID 1834972Notes

Reaction equation

HRID 1834972 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° under nitrogen is added 1,4-androstadiene-3,17-dione in dimethylsulfoxide with stirring. After 15 minutes the mixture is poured onto cold aqueous ammonium chloride. The solid which forms is rapidly filtered, washed well with water and dissolved in ether. The ether solution is washed with water, dried over sodium sulfate and evaporated at room temperature to yield 1,5-androstadiene-3,17-dione.

Workup

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

Sources & evidence

ORD record
ord-32915c2de79942ee92ff709b776d714c
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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