2,6-Lutidine → HCID 68885000, compound

Participants

Reaction Conditions

Reaction Steps

To a −60° C. of 2,6-dimethyl-pyridine (48.3 mL, 457 mmol, 1.1 equiv) was slowly added n-butyl lithium (183 mL, 2.5 M in hexane, 457 mmol, 1.1 equiv) over 30 minutes. The resulting red solution was stirred at −60° C. for an additional hour, and then treated with a solution of benzo[1,3]dioxole-5-carboxylic acid methoxy-methyl-amide (˜415 mmol) in THF (200 mL) over 1 hour. The reaction was slowly warmed to −20° C. over 3 hours, and then poured into ice (1 kg). The liquid layer was decanted and then washed with brine (3×100 mL), dried over magnesium sulfate, and concentrated in vacuo. Recrystallization from toluene provided 1-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone (57 g, 54% over two steps).

Provenance & Evidence