Dimethylformamide → 1-[(4-Methoxyphenyl)methyl]-4-phenyl-1H-imidazole-2-carbaldehyde

HRID 2252043Notes

Reaction equation

HRID 2252043 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[CH:9]2)=[CH:5][CH:4]=1.C([Li])CCC.CN([CH:29]=[O:30])C.[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[C:9]2[CH:29]=[O:30])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 17981766HCID 17981766, compoundHCID 178418339Butyllithium

Product 1

HCID 179818001-[(4-Methoxyphenyl)methyl]-4-phenyl-1H-imidazole-2-carbaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-methoxybenzyl)-4-phenylimidazole (2.00 g, 7.56 mmol) in THF (20 mL) cooled to −78° C. under nitrogen add dropwise a solution of n-butyl lithium (1.6 M hexane, 5.60 mL, 8.96 mmol). Stir the mixture at this temperature for 10 minutes then add DMF (1.43 mL, 18.5 mmol) dropwise, and continue stirring for 30 minutes. Add a saturated aqueous solution of NH4Cl (50 mL), raise the temperature to room temperature, and extract the aqueous layer with CH2Cl2 (150 mL), dry (Na2SO4), and concentrate in vacuo. Purify the residue by flash chromatography (SiO2, hexane/EtOAc 9:1) to provide 1.75 g (79% yield). MS(ES+): m/z=293 (M+H)+

Workup

  1. extractionextract the aqueous layer with CH2Cl2 (150 mL)
  2. dry with materialdry (Na2SO4)
  3. concentrationconcentrate in vacuo
  4. customPurify the residue by flash chromatography (SiO2, hexane/EtOAc 9:1)
  5. customto provide 1.75 g (79% yield)

Sources & evidence

ORD record
ord-7c2f903c627545abbb04b536d0fad39d
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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