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

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Reaction Steps

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)+

Provenance & Evidence