Dimethyl Sulfide → 4-Chlorostilbene oxide

HRID 1941468Notes

Reaction equation

HRID 1941468 reaction equation
CSC.[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[C:13]1([CH:19]=[N+]=[N-])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]2[CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10]2)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 77264-ChlorobenzaldehydeHCID 136601Benzene, (diazomethyl)-

Product 1

HCID 6085114-Chlorostilbene oxideYield 46%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of dimethyl sulphide (0.1 mmol), rhodium (II) acetate (0.01 mmol) and p-chlorobenzaldehyde (1 mmol) in dichloromethane (4 ml) was added a solution of phenyldiazomethane (1 mmol in 6 ml of tert-butylmethyl ether) at room temperature over a period of 24 hours. After addition was completed the solvent was removed in vacuo and the residue was chromatographed over silica to provide the title oxirane in 46% yield.

Workup

  1. additionAfter addition
  2. customwas removed in vacuo
  3. customthe residue was chromatographed over silica

Sources & evidence

ORD record
ord-a5f05f5c99114cd783edba35bef19355
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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