Ethanol → 17alpha-(4'-Chlorobenzylthio)-1,4-Androstadiene-3,11-Dione

HRID 2052256Notes

Reaction equation

HRID 2052256 reaction equation
[Na].C(O)C.[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][SH:11])=[CH:8][CH:7]=1.CS(O[C@H:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:35]([C:36](=[O:38])[CH2:37][C@:20]12[CH3:21])[C@:33]1([CH3:34])[C:28](=[CH:29][C:30](=[O:39])[CH:31]=[CH:32]1)[CH2:27][CH2:26]3)(=O)=O>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][S:11][C@@H:19]2[CH2:24][CH2:23][C@H:22]3[C@H:25]4[C@H:35]([C:36](=[O:38])[CH2:37][C@:20]23[CH3:21])[C@:33]2([CH3:34])[C:28](=[CH:29][C:30](=[O:39])[CH:31]=[CH:32]2)[CH2:27][CH2:26]4)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 804094-Chlorobenzyl mercaptanHCID 5360545SodiumHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

Product 1

HCID 2280985017alpha-(4'-Chlorobenzylthio)-1,4-Androstadiene-3,11-Dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1.38 gm. of sodium metal dissolved in 120 ml. of ethanol is added 6 ml. of 4-chlorobenzylmercaptan followed by 2.26 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat at reflux for 96 hours. Obtain a residue in a manner similar to that described in Example 1A. Dissolve the residue in a minimum amount of chloroform and pass through a 200 gm. silica gel column. Elute with chloroform following the fractions by TLC. Combine the fractions, reduce, and crystallize the residue from ethyl acetate/hexane to obtain the title compound; m.p. 176°-180° C.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 96 hours
  3. customObtain a residue in a manner similar to
  4. washElute with chloroform following the fractions by TLC
  5. customcrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2b114f12da4544d1b823c737c2d6fe27
Source dataset
uspto-grants-1980_01
Patent number
US04183924

Reaction notes

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