2-Methylimidazole → 4-(2-Methyl-1H-imidazol-1-yl)benzaldehyde

To a suspension of NaH (0.612 g, 15.3 mmol : 60% suspension of mineral oil) of in dry DMF (10 ml) cooled to 10° C. was added a DMF (8 ml) solution of 2-methylimidazole (1.23 g, 15 mmol) under a nitrogen atmosphere, and the mixture was stirred for 30 min at room temperature. 4-Fluorobenzaldehyde (1.90 g, 15.3 mmol) was added to the reaction mixture, and the resulting solution was stirred for 14 h. The reaction mixture was poured into an ice-cold saturated aqueous NH4Cl solution (100 ml) and extracted with ethyl acetate (100 ml×2). The organic layer was washed with water (100 ml) and brine (80 ml), dried over MgSO4 and the solvent removed under reduced pressure. The resultant residue was purified by column chromatography (SiO2 ; hexane:ethyl acetate=1:1 then ethyl acetate) to give crude 4-(2-methylimidazol-1-yl)-benzaldehyde (1.0 g), which was used without further purification.

1. stirringthe resulting solution was stirred for 14 h
2. extractionextracted with ethyl acetate (100 ml×2)
3. washThe organic layer was washed with water (100 ml) and brine (80 ml)
4. dry with materialdried over MgSO4
5. customthe solvent removed under reduced pressure
6. customThe resultant residue was purified by column chromatography (SiO2

ORD record

ord-083e4b7aaf344ee7a67681396c9378a1

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753682