3-(3-Chlorophenyl)-alpha-(4-methylphenyl)-2,1-benzisoxazole-5-methanol → [3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methylphenyl)-methanone

HRID 1788057Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of intermediate 18 (0.071 mol) and MnO2 (0.287 mol) in 1,4-dioxane (250 ml) was stirred at 80° C. for 2 hours, then cooled to room temperature, filtered over celite and washed with DCM. The solvent was evaporated till dryness, yielding 24.7 g (100%) of [3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl](4-methylphenyl)-methanone (intermediate 19).

Workup

temperaturecooled to room temperature
filtrationfiltered over celite
washwashed with DCM
customThe solvent was evaporated till dryness

Sources & evidence

ORD record: ord-b8c3594ec5a64ca4a578b8f45428384d
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511138B2

Reaction notes

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