Benzaldehyde → Stilbene oxide

HRID 1941473Notes

Reaction equation

HRID 1941473 reaction equation
[C:1]1([CH:7]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:1]1([CH:7]2[O:19][CH:12]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 136601Benzene, (diazomethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 28649Stilbene oxideYield 58%

Reagents, catalysts & solvents 2

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

Procedure

Phenyl diazomethane (1 mmol in 6 ml of t-butylmethylether) was added to a stirred solution of a sulphide of formula (B) wherein R' is hydrogen (0.2 mmol), rhodium (II) acetate (4.0 mg, 0.01 mmol) and benzaldehyde (1 mmol) in dichloromethane (4 ml) at room temperature over a period of 24 hours. After the addition was complete the solvent was removed in vacuo and the residue was chromatographed over silica [eluent dichloromethane:petrol (2:3)] to give the titled compound in 58% yield and 11% ee.

Workup

  1. customat room temperature
  2. customof 24 hours
  3. additionAfter the addition
  4. customwas removed in vacuo
  5. customthe residue was chromatographed over silica [eluent dichloromethane:petrol (2:3)]

Sources & evidence

ORD record
ord-7c80eec67a9c44569f07a42c0ae4603b
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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