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

HRID 1777369Notes

Reaction equation

HRID 1777369 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[C:17]([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:16]=[CH:15][C:14]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>ClCCl>[Cl:12][C:13]1[CH:18]=[C:17]([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:16]=[CH:15][C:14]=1[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 70869544{4-[5-(2-Chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]-phenyl}-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 867151454-[5-(2-Chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridiniumchlorochromate (3.6 g, 0.017 mol) is added to a solution of {4-[5-(2-chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]-phenyl}-methanol (4.0 g, 0.011 mol) in dichloromethane (40 mL). The reaction mixture is stirred at room temperature for 30 minutes, filtered and washed with dichloromethane (40 mL). Filtrate is concentrated under reduced pressure to give crude which is purified by column chromatography (230; 400 mesh: 9.5:0.5 toluene:ethyl acetate) to yield 4-[5-(2-chlorobiphenyl-4-yl)-[1,2,4]-oxadiazol-3-yl]-benzaldehyde.

Workup

  1. filtrationfiltered
  2. washwashed with dichloromethane (40 mL)
  3. concentrationFiltrate is concentrated under reduced pressure
  4. customto give crude which
  5. customis purified by column chromatography (230; 400 mesh: 9.5:0.5 toluene:ethyl acetate)

Sources & evidence

ORD record
ord-d7a052f0dc084490a71bb912ab50e8a8
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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