Hydrochloric Acid → HCID 118222766, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at −40° C. was added n-butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to −20° C. over 20 minutes. After cooling to −78° C., 4-butyl-1-methyl-1H-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at −78° C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3×20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give 1-methyl-4-propyl-1H-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization.

Provenance & Evidence