Formaldehyde → 3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol

HRID 457387Notes

Reaction equation

HRID 457387 reaction equation
[CH2:1]([N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:7]=[C:6]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH3:4].[CH2:24]=[O:25]>C(O)(=O)C>[CH2:1]([N:5]1[C:9]([CH2:24][OH:25])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:7]=[C:6]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 588180333-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazole

Product 1

HCID 588180923-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a 150 ml sealed flask is added 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazole (10.72, 35 mmol) followed by the addition of 24 ml of acetic acid and 24 ml of 37% formaldehyde, the resulting mixture is stirred at 70° C. for 8 h, then cooled to room temperature. The organic solvents is evaporated, the residue is diluted 100 ml of water and basified with sodium hydroxide solution, the mixture is extracted with ethyl acetate (100 ml×4), washed with water and brine, dried over Na2SO4 Concentration and purification through silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 1:1) affords 10.0 of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol as white solid. 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, dd, J=8.7 Hz), 7.354˜7.51(2H, m), 7.44˜7.38 (3H, m), 6.87 (2H, d, J=8.7 Hz), 4.59 (2H, s), 3.95 (2H, t, J=7.5 Hz), 3.784 (3H, s), 1.60 (2H, m), 1.16 (2H, m), 0.77 (3H, t, J=7.2 Hz); MS (+VE) m/z 337(M+1).

Workup

  1. customTo a 150 ml sealed flask
  2. temperaturecooled to room temperature
  3. customThe organic solvents is evaporated
  4. additionthe residue is diluted 100 ml of water
  5. extractionthe mixture is extracted with ethyl acetate (100 ml×4)
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4 Concentration and purification through silica gel chromatography (hexanes/ethyl acetate, from 8:1 to 1:1)

Sources & evidence

ORD record
ord-824e94b9ed8742829a78bccd1425cfd0
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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