(1-Methyl-4-phenyl-1H-imidazol-5-YL)methanol → 1-Methyl-4-phenyl-1H-imidazole-5-carbaldehyde

HRID 32508Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=[CH:3]1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]=[CH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

Manganese dioxide (11.5 g) was added to a suspension of (1-methyl-4-phenyl-1H-imidazol-5-yl)methanol (intermediate 1) (5.75 g) in dioxane (100 mL), and the resulting mixture heated to 80° C. for 8 hours, and allowed to cool to ambient temperature overnight. The mixture was reheated to 80° C., filtered through diatomaceous earth and the cake washed well with acetone. Purification by flash chromatography on silica eluting with EtOAc:hexane (50:50 to 100:0) gave the title compound (4.90 g, 86%) as a pale solid.

Workup

temperatureto cool to ambient temperature overnight
customwas reheated to 80° C.
filtrationfiltered through diatomaceous earth
washthe cake washed well with acetone
customPurification by flash chromatography on silica eluting with EtOAc:hexane (50:50 to 100:0)

Sources & evidence

ORD record: ord-f12a798dfa6b4d949c5c57ecaa2d9ced
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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