Hexane → 6-Chloropyridine-3-carbaldehyde

Participants

Reaction Steps

At −78° C., a hexane solution (11.5 mL) of 1.59 M n-butyllithium was dropwise added to a diethyl ether solution (140 mL) of 5-bromo-2-chloropyridine (2.9 g). This was stirred at that temperature, then a diethyl ether solution (3 mL) of DMF (1.8 mL) was added thereto and stirred at that temperature for 3.5 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/9) to obtain the entitled compound (1.4 g).

Provenance & Evidence