Ammonium Chloride → 1-(2,6-Dichloro-pyridin-4-yl)-3,3-diphenyl-propan-1-one

Participants

Reaction Conditions

Reaction Steps

At −70° C. to a solution of 2,6-dichloro-4-iodopyridine (1.02 g) in THF (20 mL) was added n-BuLi (1.6 M in hexane, 2.3 mL) dropwise. The mixture was stirred for additional 15 min at which timepoint a solution of N-methoxy-N-methyl-3,3-diphenyl-propionamide (200 mg) in THF (10 mL) was added. The reaction mixture was stirred for 1 hour at −70° C. A saturated aqueous solution of NH4Cl 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. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:10) to yield 1-(2,6-dichloro-pyridin-4-yl)-3,3-diphenyl-propan-1-one (465 mg, 88%) as a yellow oil, which was directly subjected to the next step.

Provenance & Evidence