Benzyl mercaptan → HCID 56624110, compound

HRID 2052260Notes

Reaction equation

HRID 2052260 reaction equation
[Na].[CH2:2]([SH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[C@H:15]1[CH2:20][CH2:19][C@H:18]2[C@H:21]3[C@H:31]([CH2:32][CH2:33][C@:16]12[CH3:17])[C@:29]1([CH3:30])[C:24](=[CH:25][C:26](=[O:34])[CH:27]=[CH:28]1)[CH2:23][CH2:22]3)(=O)=O.[OH-].[Na+]>C(O)C>[CH2:2]([S:9][C@@H:15]1[CH2:20][CH2:19][C@H:18]2[C@H:21]3[C@H:31]([CH2:32][CH2:33][C@:16]12[CH3:17])[C@:29]1([CH3:30])[C:24](=[CH:25][C:26](=[O:34])[CH:27]=[CH:28]1)[CH2:23][CH2:22]3)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 56611918HCID 56611918, compound

Product 1

HCID 56624110HCID 56624110, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.25 gm. of sodium metal dissolved in 185 ml. of ethanol is added 8.2 ml. of benzyl mercaptan followed by 3 gm. of 17β-methanesulfonyloxy-1,4-androstadiene-3-one. The reactants are heated to reflux for 48 hours. Pour the reaction mixture into 5% NaOH solution and extract with ethyl acetate. Wash the ethyl acetate extracts with water, dry over Na2SO4, and evaporate to a residue. The residue is purified on a 300 gm. silica gel column eluting with chloroform/ethyl acetate (2:1) to obtain the title compound.

Workup

  1. temperatureThe reactants are heated
  2. temperatureto reflux for 48 hours
  3. extractionextract with ethyl acetate
  4. washWash the ethyl acetate
  5. dry with materialdry over Na2SO4
  6. customevaporate to a residue
  7. customThe residue is purified on a 300 gm
  8. washsilica gel column eluting with chloroform/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-068b38363b3048f2a247939c3fb81df1
Source dataset
uspto-grants-1980_01
Patent number
US04183924

Reaction notes

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