[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol → 1-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde

HRID 72716Notes

Reaction equation

HRID 72716 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

HCID 71114420[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanol

Product 1

HCID 867125651-(4-ethylphenyl)-1H-imidazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

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).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe filter pad was washed with dichloromethane
  3. dry with materialThe combined filtrates were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. customto afford the product

Sources & evidence

ORD record
ord-f7f406a1e30c4379ac429d67cc2b456e
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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