(4-(5-(2'-Methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol → 4-(5-(2'-Methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde

HRID 2404362Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][C:9]=1[C:27]([F:30])([F:29])[F:28]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][C:9]=1[C:27]([F:30])([F:28])[F:29]

Participants

Conditions

Temperature: 70 °C

Procedure

(4-(5-(2′-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (5.89 g, 14.4 mmol) was dissolved in dioxane (100 mL) and manganese dioxide (10 g, 116.0 mmol) was added. The mixture was heated at 70° C. overnight and then the solvent was removed in vacuo. The residue was triturated with a mixture of petrol/diethyl ether to give the title compound as a white solid (5.72 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 10.13 (1H, s), 8.64 (1H, s), 8.43-8.36 (3H, m), 8.06 (2H, d, J=8.0 Hz), 7.49 (1H, d, J=8.0 Hz), 7.38-7.21 (3H, m), 7.15 (1H, d, J=7.6 Hz), 2.07 (3H, s). LC/MS (Method A): 409 (M+H)+. HPLC (Method G) Rt 4.89 min (Purity: 95.7%).

Workup

customthe solvent was removed in vacuo
customThe residue was triturated with a mixture of petrol/diethyl ether

Sources & evidence

ORD record: ord-b3230d70e8014a5182aeb49cecf764f2
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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