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

HRID 1028191

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-IH-imidazol-5-yl)methanol, (Intermediate 6) (2.4 g, 7.4 mmol) in CH2Cl2 (60 mL) was treated with manganese (IV) oxide, activated (commercially available from Aldrich): MnO2 (2.8 g, 32.3 mmol) at room temperature. The mixture was heated at 60° C. for 2 hours. The mixture was then cooled to room temperature 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)(I-trityl-IH-imidazol-5-yl)methanone, (Intermediate 7), 1.48 g, (62%).

Workup

customat room temperature
temperatureThe mixture was then cooled to room temperature
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-c45a482b5fd34f4d9eec292f8ecdaef2
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735438B2

Linked notes

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