[5-(3-Chlorophenyl)isoxazol-3-yl]methanol → 5-(3-Chlorophenyl)isoxazole-3-carbaldehyde

HRID 1453799Notes

Reaction equation

HRID 1453799 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH2:13][OH:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 57528605[5-(3-Chlorophenyl)isoxazol-3-yl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 532992685-(3-Chlorophenyl)isoxazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[5-(3-chlorophenyl)isoxazol-3-yl]methanol (178.6 g, 852 mmol) in dichloromethane (2 L) was dropwise added to pyridinium chlorochromate (400 g, 1.86 mol) in dichloromethane (2 L). The resulting slurry was stirred over night at room temperature. The slurry was filtrated through celite and the filtrate was distilled off. To the remaining solution EtOAc was added. The organic layer was washed with water, saturated brine and concentrated, to give crude title compound, which was used directly in the next step. 1H NMR (DMSO-d6): 10.13 (s, 1H), 8.08 (br s, 1H), 7.95 (m, 1H), 7.61 (m, 3H). MS (M++1)=208.

Workup

  1. filtrationThe slurry was filtrated through celite
  2. distillationthe filtrate was distilled off
  3. additionTo the remaining solution EtOAc was added
  4. washThe organic layer was washed with water, saturated brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd8591676e444695b60938888a2b7796
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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