Triethylamine → HCID 58047403, compound

Participants

Reaction Steps

To a solution of (2-fluoropyridin-4-yl)methanol (5.06 g, 39.8 mmol) in DMF (100 mL) were added triethylamine (8.30 mL, 59.7 mmol) and methanesulfonyl chloride (3.08 mL, 39.8 mmol) under ice-cooling. After stirring for 30 min, 4-ethoxyphenol (5.77 g, 41.8 mmol) and potassium carbonate (5.50 g, 39.8 mmol) were added thereto and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added ethyl acetate, and the mixture was washed with water, 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3). A mixture of the obtained product and 4-ethoxyphenol (starting material) was purified again by basic silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give the title compound (822 mg, yield 8.4%).

Provenance & Evidence