3-[3-Chloro-4-(hydroxymethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole → 2-Chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehyde

HRID 885800Notes

Reaction equation

HRID 885800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 866315523-[3-Chloro-4-(hydroxymethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazoleHCID 178418287HCID 178418287, compound

Product 1

HCID 866315512-Chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehydeYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a solution of 2.0 g of 3-[3-chloro-4-(hydroxymethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 60 mL of dichloromethane, 4.0 g of silica gel and 1.3 g of pyridinium chlorochromate were added, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was filtered through glass filter in which silica gel was packed to separate a solid with a solvent. The solvent was distilled off under reduced pressure. The residual solid was washed with diisopropyl ether to obtain 1.45 g of the aimed product as pale yellow crystal.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered through glass
  3. filtrationfilter in which silica gel
  4. customto separate a solid with a solvent
  5. distillationThe solvent was distilled off under reduced pressure
  6. washThe residual solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-615d3869caba4cdb9dba9d11685f3632
Source dataset
uspto-grants-2012_08
Patent number
US08242283B2

Reaction notes

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