Hexane → 6-Chloropyridine-3-carbaldehyde

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).

1. stirringstirred at that temperature for 3.5 hours
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with saturated saline water
4. dry with materialdried with anhydrous magnesium sulfate
5. customthe solvent was evaporated off under reduced pressure
6. customThe resulting residue was purified through silica gel column chromatography (ethyl acetate/hexane=1/9)

ORD record

ord-c9fa80da37d745b18414bf52fd34a3b5

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566781B2