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

HRID 2242247Notes

Reaction equation

HRID 2242247 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:28]=[C:29]([CH2:33][OH:34])[CH:30]=[CH:31][CH:32]=3)[N:23]=2)=[CH:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14]>C(Cl)Cl>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([C:22]2[O:26][N:25]=[C:24]([C:27]3[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=3)[CH:33]=[O:34])[N:23]=2)=[CH:20][CH:21]=1)[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 59204314{3-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 592043053-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Florosil (400 mg) and pyridinium chlorochromate (195 mg, 0.903 mmol) were added to a solution of {3-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]phenyl}methanol (139 mg, 0.451 mmol) and methylene chloride (2.5 mL) and stirred at ambient temperature for 3 hours. The reaction mixture was filtered through a pad of silica gel. The pad was rinsed with methylene chloride (2×) and 1:1 ethyl acetate:hexanes (2×). The filtrate was concentrated in vacuo to give the desired compound as a crude residue.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washThe pad was rinsed with methylene chloride (2×) and 1:1 ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e64695838ae84c94b35222e08b49b17d
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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