2-Phenylethanethiol → 17alpha-(beta-Phenylethylthio)-1,4-Androstadiene-3,11-Dione

HRID 2052254Notes

Reaction equation

HRID 2052254 reaction equation
[Na].[C:2]1([CH2:8][CH2:9][SH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O[C@H:16]1[CH2:21][CH2:20][C@H:19]2[C@H:22]3[C@H:32]([C:33](=[O:35])[CH2:34][C@:17]12[CH3:18])[C@:30]1([CH3:31])[C:25](=[CH:26][C:27](=[O:36])[CH:28]=[CH:29]1)[CH2:24][CH2:23]3)(=O)=O>C(O)C>[C:2]1([CH2:8][CH2:9][S:10][C@@H:16]2[CH2:21][CH2:20][C@H:19]3[C@H:22]4[C@H:32]([C:33](=[O:35])[CH2:34][C@:17]23[CH3:18])[C@:30]2([CH3:31])[C:25](=[CH:26][C:27](=[O:36])[CH:28]=[CH:29]2)[CH2:24][CH2:23]4)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 781262-PhenylethanethiolHCID 5360545SodiumHCID 5660910317beta-Methanesulfonyloxy-1,4-androstadiene-3,11-dione

Product 1

HCID 5661854417alpha-(beta-Phenylethylthio)-1,4-Androstadiene-3,11-Dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.25 gm. of sodium metal dissolved in 180 ml. of ethanol is added 8 ml. of β-phenylethyl mercaptan followed by 3 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3,11-dione. Heat the reaction at reflux for 48 hours. Obtain a residue in a manner similar to that described in Example 1A. Chromatograph the residue on a 300 gm. silica gel column eluting with chloroform/ethyl acetate (2:1). Combine the desired fractions as determined by thin layer chromatography, evaporate and crystallize the resultant residue from ether/hexane to obtain the title compound; m.p. 112°-115° C.

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux for 48 hours
  4. customObtain a residue in a manner similar to
  5. washsilica gel column eluting with chloroform/ethyl acetate (2:1)
  6. customevaporate
  7. customcrystallize the resultant residue from ether/hexane

Sources & evidence

ORD record
ord-898fd763bdf844b5afc955f7d22c9b83
Source dataset
uspto-grants-1980_01
Patent number
US04183924

Reaction notes

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