(2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanol → (2,3-Dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanone

HRID 1516607Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[N:15]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[N:13][CH:12]=1)[OH:10]>C(Cl)Cl.[O-2].[Mn+4].[O-2].O=[Mn]=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[N:15]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:14]=[N:13][CH:12]=1)=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (2,3-dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 2) (2.3 g, 5.18 mmol) in CH2Cl2 (40 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (4.5 g, 52 mmol) at rt. The mixture was heated to 60° C. for 2 h. The mixture was then cooled to rt and filtered through celite and the solvent was removed under vacuum. The residue was purified by MPLC with 3 to 5% MeOH:CH2Cl2 to give (2,3-dimethylphenyl)(1-trityl-1H-imidazol-5-yl)methanone, (Intermediate 3) (2.2 g, 96%).

Workup

customat rt
temperatureThe mixture was then cooled to rt
filtrationfiltered through celite
customthe solvent was removed under vacuum
customThe residue was purified by MPLC with 3 to 5% MeOH

Sources & evidence

ORD record: ord-caca0991eebb49049c8c382f779bf8ad
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227499B2

Reaction notes

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