Ammonium Chloride → 19-t-Butyldimethylsiloxy-5-androstene-3,17-dione

HRID 1390769Notes

Reaction equation

HRID 1390769 reaction equation
CC(C)([O-])C.[K+].[O:7]([CH2:15][C@@:16]12[C@@H:33]3[C@H:24]([C@H:25]4[C@@:29]([CH2:31][CH2:32]3)([CH3:30])[C:28](=[O:34])[CH2:27][CH2:26]4)[CH2:23][CH2:22][C:21]1=[CH:20][C:19](=[O:35])[CH2:18][CH2:17]2)[Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[Cl-].[NH4+]>CS(C)=O>[O:7]([CH2:15][C@@:16]12[C@@H:33]3[C@H:24]([C@H:25]4[C@@:29]([CH2:31][CH2:32]3)([CH3:30])[C:28](=[O:34])[CH2:27][CH2:26]4)[CH2:23][CH:22]=[C:21]1[CH2:20][C:19](=[O:35])[CH2:18][CH2:17]2)[Si:8]([C:11]([CH3:14])([CH3:12])[CH3:13])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1057397419-t-Butyldimethylsiloxy-4-androstene-3,17-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 7060535419-t-Butyldimethylsiloxy-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-t-butyldimethylsiloxy-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 dissolved in ether. The ether solution is washed well with water and dried over sodium sulfate. Evaporation of the ether at room temperature yields 19-t-butyldimethylsiloxy-5-androstene-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 well with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the ether at room temperature

Sources & evidence

ORD record
ord-21682b6fe8f145579e7cea153904d296
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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