Sodium hydride → HCID 68428230, compound

Participants

Reaction Steps

To a solution of 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (15 g, 97.3 mmol) in 124 mL of N,N′-dimethylformamide at 0° C. was added sodium hydride (60% dispersion in mineral oil, 4.66 g, 2.80 mmol). The ice bath was then removed, and the reaction mixture was stirred at ambient temperature for 10 min. After the reaction mixture was cooled at 0° C., 1-bromo-3-methylbutane was added. The ice bath was removed, and the reaction mixture was stirred at ambient temperature for 2 hours. Saturated ammonium chloride aqueous solution (200 mL) and ethyl acetate (600 mL) were added to quench the reaction. The organic layer was washed with water and saturated sodium chloride aqueous solution, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-30% ethyl acetate in hexanes to afford 18.3 g of the title compound as a colorless oil. MS: (+) m/z 224.4 (M+1).

Provenance & Evidence