Ammonium Chloride → HCID 117770008, compound

Temperature

-78 °C

To a suspension of 2-bromo-5-iodopyridine (2.00 g) in tetrahydrofuran (20 mL) and diethyl ether (10 mL) was added dropwise 1.6M n-butyllithium hexane solution (4.40 mL) at −78° C. The mixture was stirred at −78° C. for 30 min under argon atmosphere, and a solution of tetrahydro-4H-pyran-4-one (0.651 mL) in tetrahydrofuran (10 mL) was added dropwise thereto at −78° C. The reaction mixture was slowly warmed to −50° C., aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed successively 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 (0.932 g).

1. customat −78° C
2. temperatureThe reaction mixture was slowly warmed to −50° C.
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed successively 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-70c536cde5314cde9557ebae6e7062b7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085578B2