Chloride → HCID 14403425, compound

HRID 1089893Notes

Reaction equation

HRID 1089893 reaction equation
[Cl-].[C:2]1([S:8][C:9]2([C:12]([CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:13])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C1(C)C=CC=CC=1>[C:2]1([S:8][C:9]2([C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[O:13])[CH2:10][CH2:11]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 312ChlorideHCID 53893725HCID 53893725, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14403425HCID 14403425, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

460 mg (0.5 mmol) of tris-triphenylphosphinerhodium chloride (=1 mol-%, with respect to the reaction component) are added to a 100 ml autoclave. After purging with nitrogen, an air-free solution of 15.7 g (0.05 mol) of 4-chlorophenyl-ethenyl 1-phenylmercapto-cyclopropyl ketone in 40 ml of toluene is added and the mixture is heated to 50° C. under a hydrogen pressure of 30 bar. The hydrogen pressure is held between 40 and 50 bar until gas uptake has ended. The mixture is then reacted for a further hour. For working up, the solvent is stripped off under reduced pressure and the residue remaining is purified on silica gel using dichloromethane as eluant. 14.2 g (90% of theory) of 4-chlorophenylethyl 1-phenylmercaptocyclopropyl ketone are obtained in the form of an oily product.

Workup

  1. customAfter purging with nitrogen
  2. customThe mixture is then reacted for a further hour
  3. customthe residue remaining is purified on silica gel

Sources & evidence

ORD record
ord-a5774997c8ca40caae5bf477815c3420
Source dataset
uspto-grants-1992_01
Patent number
US05079374

Reaction notes

Loading…