Ammonium Chloride → 19-Trimethylsiloxy-5-androstene-3,17-dione

HRID 1390778Notes

Reaction equation

HRID 1390778 reaction equation
CC(C)([O-])C.[K+].[CH3:7][Si:8]([CH3:32])([CH3:31])[O:9][CH2:10][C@@:11]12[C@@H:28]3[C@H:19]([C@H:20]4[C@@:24]([CH2:26][CH2:27]3)([CH3:25])[C:23](=[O:29])[CH2:22][CH2:21]4)[CH2:18][CH2:17][C:16]1=[CH:15][C:14](=[O:30])[CH2:13][CH2:12]2.[Cl-].[NH4+]>CS(C)=O>[CH3:31][Si:8]([CH3:7])([CH3:32])[O:9][CH2:10][C@@:11]12[C@@H:28]3[C@H:19]([C@H:20]4[C@@:24]([CH2:26][CH2:27]3)([CH3:25])[C:23](=[O:29])[CH2:22][CH2:21]4)[CH2:18][CH:17]=[C:16]1[CH2:15][C:14](=[O:30])[CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2280149719-Trimethylsiloxy-4-androstene-3,17-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 2280690519-Trimethylsiloxy-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 a solution of 19-trimethylsiloxy-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 so obtained is rapidly filtered, washed well with water and dissolved in ether. The ether solution is washed well with water, dried over sodium sulfate and the ether removed at room temperature to yield 19-trimethylsiloxy-5-androstene-3,17-dione.

Workup

  1. customThe solid so obtained
  2. filtrationis rapidly filtered
  3. washwashed well with water
  4. dissolutiondissolved in ether
  5. washThe ether solution is washed well with water
  6. dry with materialdried over sodium sulfate
  7. customthe ether removed at room temperature

Sources & evidence

ORD record
ord-7556aac09f0749edba5d1042d9c03f41
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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