Water → (6-Chloropyridin-2-yl)acetonitrile

Temperature

-78 °C

To a solution of acetonitrile (2.77 mL) in tetrahydrofuran (80 mL) was added dropwise n-butyl lithium hexane solution (1.6 M, 29.6 mL) at −78° C., and the reaction mixture was stirred at −78° C. for 1 hr under argon atmosphere. A solution of 2,6-dichloropyridine (2.0 g) in tetrahydrofuran (10 mL) was added dropwise thereto at −78° C., and the reaction mixture was stirred at −78° C. for 2 hr under argon atmosphere, and allowed to be warmed to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.91 g).

1. stirringat −78° C., and the reaction mixture was stirred at −78° C. for 2 hr under argon atmosphere
2. temperatureto be warmed to room temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-e6c479666a6d445da40f4c8ea1bdecac

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085578B2