Acetonitrile → HCID 583430、化合物

温度

78 °C

To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl) acetonitrile (6.2 g, yield 80%). 1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1 H), 7.32 (d, J=6.0 Hz, 1 H), 3.90 (s, 2H), 2.40 (s, 3H).

1. waitThe reaction mixture was kept at minus 78° C. for 1 hour
2. temperaturewarmed up slowly to room temperature
3. stirringstirred for another hour
4. customthe layer was separated
5. washThe organic layer was washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customto give 18 g of crude product
10. customThe crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1)

ORDレコード

ord-7d75eddfaa1a4d4c9c196f8ef4b68c06

出典データセット

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09072313B2