Water → 1-(4-Methoxybenzyl)-4-phenyl-1H-imidazole-5-carbaldehyde

HRID 32539Notes

Reaction equation

HRID 32539 reaction equation
C[O:2][CH:3](OC)[C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=[N:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C(O)=O>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[C:4]([CH:3]=[O:2])=[C:5]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:6]=[CH:7]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 179658085-(Dimethoxymethyl)-1-(4-methoxybenzyl)-4-phenyl-1H-imidazole2×

Product 1

HCID 179658511-(4-Methoxybenzyl)-4-phenyl-1H-imidazole-5-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

5-(Dimethoxymethyl)-1-(4-methoxybenzyl)-4-phenyl-1H-imidazole (Intermediate 29) (1.5 g) was dissolved in formic acid (10 mL) and water (10 mL) and stirred for 16 hours at ambient temperature. The solvents were evaporated in vacuo, the residue was azeotroped with toluene (2×10 mL) and the residual oil dried in vacuo over P2O5 to give the title compound as a colourless oil (1.29 g, 100%);

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was azeotroped with toluene (2×10 mL)
  3. dry with materialthe residual oil dried in vacuo over P2O5

Sources & evidence

ORD record
ord-ab7c077f2fef4eeab19b25690d4c9f4d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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