1. A solution of 4-methylpyridine (1.07 g, 11.5 mmol) in THF (10.0 mL) was added slowly and dropwise to a solution of tetrahydrofuran (THF, 20.0 mL) containing lithium diisopropylammonium (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) at -78°C.
2. The dry ice bath was removed and the reaction mixture was stirred at 0 °C for 30 min and then re-cooled to -78 °C.
3. A solution of 2-chloro-N-methoxy-N-methylbenzamide (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise to the reaction mixture.
4. The reaction mixture was gradually warmed to room temperature and stirred overnight.
5. The resulting white solid was collected by filtration and dissolved in ethyl acetate.
6. The organic phase was washed sequentially with water and brine and then dried with anhydrous magnesium sulfate.
7. Vacuum concentration of the dried organic phase afforded the target product 1-(2-chlorophenyl)-2-(pyridin-4-yl)ethanone (1.09 g, 4.7 mmol, 47% yield) as a white solid.
