{4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanol → 4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

HRID 2242243Notes

Reaction equation

HRID 2242243 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][CH:25]=3)[N:20]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 59204295{4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 592042754-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Florosil (250 mg) and PCC (121.5 mg, 0.564 mmol) was added to a solution of {4-[5-(4-methylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanol (75.1 mg, 0.282 mmol) and CH2Cl2 (1.5 mL) and stirred at room temperature for 3 hours. The reaction mixture was diluted with CH2Cl2 and filtered through a pad of silica gel. The pad was eluted with CH2Cl2 and 1:1 ethyl acetate:hexanes and the combined eluents were concentrated in vacuo to provide the title compound as a crude residue.

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washThe pad was eluted with CH2Cl2 and 1:1 ethyl acetate
  3. concentrationhexanes and the combined eluents were concentrated in vacuo

Sources & evidence

ORD record
ord-af12f56b6be64099960add444208b27e
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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