4-benzyloxy-2-(1-hydroxyethyl)-1-methyl-1H-benzimidazole → 2-acetyl-4-benzyloxy-1-methyl-1H-benzimidazole

HRID 636500Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH:18]([OH:20])[CH3:19])[N:14]([CH3:21])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[C:18]([C:15]1[N:14]([CH3:21])[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:17]=2[N:16]=1)(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-benzyloxy-2-(1-hydroxyethyl)-1-methyl-1H-benzimidazole (87.0 mg) in dichloromethane (3 ml) was added manganese dioxide (870 mg) at 0° C. under nitrogen atmosphere, and the mixture was stirred for 30 minutes at 0° C. and then for 1.5 hours at ambient temperature. The reaction mixture was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:1, v/v) to give 2-acetyl-4-benzyloxy-1-methyl-1H-benzimidazole (74.2 mg).

Workup

waitfor 1.5 hours at ambient temperature
customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record: ord-dbfc3935cd834daeb4eb816c7d7ccc48
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194396B1

Reaction notes

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