Ammonium Chloride → 19-Tetrahydropyranyloxy-1,5-androstadiene-3,17-dione

HRID 1390736Notes

Reaction equation

HRID 1390736 reaction equation
CC(C)([O-])C.[K+].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][C@@:15]12[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27](=[O:33])[CH2:26][CH2:25]4)[CH2:22][CH2:21][C:20]1=[CH:19][C:18](=[O:34])[CH:17]=[CH:16]2.[Cl-].[NH4+]>CS(C)=O>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][C@@:15]12[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27](=[O:33])[CH2:26][CH2:25]4)[CH2:22][CH:21]=[C:20]1[CH2:19][C:18](=[O:34])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2280690119-Tetrahydropyranyloxy-1,4-androstadiene-3,17-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 2280690219-Tetrahydropyranyloxy-1,5-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 19-tetrahydropyranyloxy-1,4-androstadiene-3,17-dione in dimethylsulfoxide with stirring. After 15 minutes the mixture is poured onto cold aqueous solution of 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 19-tetrahydropyranyloxy-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-0e0e7384f68941c4b02dda1f7564c6c4
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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