Hydrochloric Acid → HCID 22262086, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence