Hydrochloric Acid → HCID 22262086, compound

Temperature

80 °C

To a solution of 6-fluoro-3-pyridinecarboxylic acid (9.5 g, 67.3 mmol) in tetrahydrofuran (150 ml) was added 1,1′-carbonylbis-1H-imidazole (12.0 g, 74.1 mmol), and the mixture was stirred at 80° C. for 10 min. The reaction solution was cooled to room temperature and monoethyl malonate magnesium salt (10.6 g, 37.0 mmol) was added. The mixture was stirred at room temperature for 2 hrs. To the reaction solution were added ethyl acetate (100 ml) and water (100 ml). Then, conc. hydrochloric acid was added until the aqueous layer showed acidic pH. The reaction solution was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-(6-fluoropyridin-3-yl)-3-oxopropionate (9.74 g, 68%) as a brown oil.

1. temperatureThe reaction solution was cooled to room temperature
2. stirringThe mixture was stirred at room temperature for 2 hrs
3. extractionThe reaction solution was extracted with ethyl acetate (200 ml×2)
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

ORD record

ord-fd93fec00f8c428a9cebd10616a3e133

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2