Diethyl Ether → 1-(2-Chloropyridin-4-yl)ethan-1-one

温度

0 °C

2-Chloropyridine-4-carbonitrile (250 g, 1.80 mol, 1.00 equiv) and ether (3750 mL) were combined in a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen. A solution of MeMgI in ether (1200 mL) was added dropwise with stirring at 0° C. in 30 min. The resulting solution was stirred for 6 h at room temperature and then poured into water/ice/6N hydrogen chloride (3000 mL) and stirred for 10 min. The organic phase was separated and the aqueous phase was extracted with ether (3×2000 mL). The combined organic layer was washed with brine (2×2000 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel (1:20 ethyl acetate/petroleum ether) to afford 1-(2-chloropyridin-4-yl)ethan-1-one as a light yellow solid.

1. custompurged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionA solution of MeMgI in ether (1200 mL) was added dropwise
4. stirringThe resulting solution was stirred for 6 h at room temperature
5. additionpoured into water/ice/6N hydrogen chloride (3000 mL)
6. stirringstirred for 10 min
7. customThe organic phase was separated
8. extractionthe aqueous phase was extracted with ether (3×2000 mL)
9. washThe combined organic layer was washed with brine (2×2000 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under vacuum
12. customThe residue was purified by column chromatography on silica gel (1:20 ethyl acetate/petroleum ether)

ORDレコード

ord-7b6b51882e594c518306add5ba56fa9c

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09242984B2