[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol → 1-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[CH:10]2)=[CH:5][CH:4]=1)[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([CH:14]=[O:15])=[CH:12][N:11]=[CH:10]2)=[CH:7][CH:8]=1)[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of [1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol (C18) (2.50 g, 12.4 mmol) in dichloromethane (15 mL) was treated with activated manganese(IV) oxide (96%, 11.1 g, 123 mmol), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was then filtered through Celite and the filter pad was washed with dichloromethane. The combined filtrates were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification was carried out by chromatography on silica gel (Gradient: 30% to 80% ethyl acetate in heptane) to afford the product. Yield: 1.8 g, 9.0 mmol, 73%. LCMS m/z 201.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.31 (t, J=7.6 Hz, 3H), 2.75 (q, J=7.6 Hz, 2H), 7.26-7.30 (m, 2H, assumed; partially obscured by solvent peak), 7.32-7.36 (m, 2H), 7.77 (dd, J=0.8, 0.8 Hz, 1H), 7.94 (d, J=0.9 Hz, 1H), 9.76 (d, J=0.8 Hz, 1H).