Benzyl Bromide → 1-(2,6-Dimethyl-pyridin-4-yl)-2-phenyl-ethanone

Participants

Reaction Conditions

Reaction Steps

At −78° C., to a solution of N-methoxy-2,6,N-trimethyl-isonicotinamide (1 g) and benzyl bromide (0.73 mL) in THF (30 mL) was added n-BuLi (1.6M in hexane, 6.6 mL) dropwise. The reaction was stirred at −78° C. for 3 hours. A saturated aqueous solution of NH4Cl (200 mL) was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 1:2) yielded the title compound (1.8 g, 99%) as a colorless liquid, MS (ESI+): m/z=226.1 [M+H]+.

Provenance & Evidence