Diisopropylamine → HCID 10368088, compound

Participants

Reaction Conditions

Reaction Steps

In tetrahydrofuran (20 mL) was placed diisopropylamine (1.41 mL, 10.0 mmol). The mixture was cooled to 0° C. under argon and in n-butyl lithium (4 mL of 2.5 M in toluene, 10.08 mmol) was added. The reaction was stirred at 0° C. for 0.5 hour, then cooled to -78° C. A solution of methyl 3-(3,4-methylenedioxyphenyl)propanoate (2 g, 9.6 mmol) (prepared by reaction of 3,4-methylenedioxybenzaldehyde with trimethyl phosphonoacetate in the presence of sodium hydride in ethylene glycol dimethyl ether, followed by catalytic hydrogenation with 10% palladium on carbon at 3 atmospheres of hydrogen in an ethyl acetate solution) in tetrahydrofuran (15 mL) was added, and the mixture was stirred at -78° C. for 1 hour. A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (2.49 g, 9 mmol) in tetrahydrofuran was added, and the mixture was stirred for 30 minutes at -78° C. The reaction was quenched with ammonium chloride solution, and the product was extracted into ethyl acetate. The concentrated product was flash chromatographed with 6:4 ethyl acetate/hexane to yield 1.33 g (31%) of the title compound as an oil.

Provenance & Evidence