HCID 66678519, compound → HCID 86661516, compound

HRID 2410599Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

(4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)methanol (401 mg, 1.0 mmol) was dissolved in dioxane (10 mL) and manganese dioxide (1.0 g, 11.6 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 and diethyl ether to give the title compound as a white solid (361 mg, 90%). 1H NMR (CDCl3, 400 MHz) δ 10.10 (1H, s), 8.45 (1H, s), 8.33 (1H, d, J=8.3 Hz), 8.19 (1H, dd, J=7.8, 1.9 Hz), 7.87 (2H, d, J=6.9 Hz), 7.38-7.24 (4H, m), 7.14 (1H, d, J=7.4 Hz), 4.24-4.21 (2H, m), 3.34 (3H, s), 2.81 (3H, s), 2.09 (3H, s).

Workup

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

Sources & evidence

ORD record: ord-f665192fe4e24df8be8ad7a739ae7f76
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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