HCID 53893725, compound → HCID 14403425, compound

HRID 1650730Notes

Reaction equation

HRID 1650730 reaction equation
[C:1]1([S:7][C:8]2([C:11]([CH:13]=[CH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:12])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C1(C)C=CC=CC=1>[C:1]1([S:7][C:8]2([C:11]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:12])[CH2:9][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 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) o& tris-triphenylphosphinyl rhodium chloride (=1 mol %, with respect to the reaction components) is added to a 100 ml autoclave. After purging with nitrogen, an air-free solution of 15.7 g (0.05 mol) of 4-chlorophenylethenyl 1-phenylmercapto-cyclopropyl ketone in 40 ml of toluene is added and heated at 50° C. under a hydrogen pressure of 30 bar. The hydrogen pressure is kept between 40 and 50 bar until the absorption of gas is complete. The mixture is subsequently reacted for 1 hour. For working up, the solvent is removed under reduced pressure and the residue which remains is purified on silica gel using dichloromethane as the eluant. 14.2 g (90% of theory) of 4-chlorophenylethyl 1-phenylmercaptocyclopropyl ketone are obtained in the form of an oily product.

Workup

  1. additionis added to a 100 ml autoclave
  2. customAfter purging with nitrogen
  3. customuntil the absorption of gas
  4. customThe mixture is subsequently reacted for 1 hour
  5. customthe solvent is removed under reduced pressure
  6. customthe residue which remains is purified on silica gel

Sources & evidence

ORD record
ord-658e2ba002614fd3bbcd5af5eef8592a
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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