p-Toluenesulfenyl chloride → HCID 70564755, compound

HRID 2286321Notes

Reaction equation

HRID 2286321 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21][CH3:22])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1.[C:25]1([CH3:33])[CH:30]=[CH:29][C:28]([S:31]Cl)=[CH:27][CH:26]=1>ClCCl>[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][C:14]([S:31][C:28]4[CH:29]=[CH:30][C:25]([CH3:33])=[CH:26][CH:27]=4)=[C:15]3[S:21][CH3:22])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1

Participants

4

Reactant 2

HCID 11019146p-Toluenesulfenyl chlorideHCID 14823699HCID 14823699, compound

Product 1

HCID 70564755HCID 70564755, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 900 mg of 9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one in 900 ml of dichloromethane is stirred with 500 mg of p-toluenesulfenyl chloride at room temperature under a nitrogen atmosphere for about 16 hours. The resulting solution is washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo to give 1.3 g of a solid, which is dissolved in chloroform-hexane (3:2) and chromatographed on a 50 g-silica gel column. Elution with chloroform-hexane (3:2) gives 930 mg of a tlc-homogenous material. Two crystallizations from acetone-hexane give 400 mg of an analytical specimen of the title compound, melting point 205°-206° C.

Workup

  1. washThe resulting solution is washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-548cf7bd655c49c8a575de94a11b2d89
Source dataset
uspto-grants-1981_05
Patent number
US04265815

Reaction notes

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