Sodium hydride → HCID 54415455, compound

Participants

Reaction Steps

To a mixture of NaH (80% oil dispersion, 41 mg, 1.35 mmol, previously washed with hexanes) in DMF (4 ml) was added dropwise a solution of 2-n-butyl-1-methyl-5-(2-hydroxy-4-methoxybenzoyl)-1H-imidazole (361 mg, 1.25 mmol) in DMF (3 ml) at 0° under argon. The cooling bath was removed and the mixture stirred for 20 min. at ambient temperature. t-Butyl bromoacetate (222 μl, 1.35 mmol) was added neat and the reaction stirred overnight. The mixture was partitioned between water and EtOAc and the layers separated. The aqueous layer was further extracted (EtOAc, 2x) and the combined organic extract was washed with water (5x) and brine. Evaporation under reduced pressure after drying (MgO4 anhydrous) afforded the title compound as a reddish oil (465 g, 93%).

Provenance & Evidence