Pyridine → 2-Formyl-4-methylphenyl 2-oxooxazolidine-3-carboxylate

Participants

Reaction Steps

To a 500 mL dry round bottom flask were added 2-oxazolidinone (9.13 g, 104.9 mmol), triphosgene (10.9 g, 36.7 mmol) and anhydrous THF (100 mL). The mixture was stirred in an ice-water bath, then triethylamine (15.8 mL, 115.4 mmol) was added slowly. The resulting mixture was stirred at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated. The residue was dissolved in 20 mL of CH2Cl2, and this solution was added slowly to a stirring mixture of 5-methylsalicylaldehyde (10.0 g, 73.4 mmol) and pyridine (8.5 mL, 104.9 mmol) in 30 mL of anhydrous CH2Cl2 at 0° C. After stirring at room temperature overnight, water (50 mL) and MTBE (100 mL) were added to the reaction mixture. The mixture was filtered and the solid was washed with cold water (20 mL×2), followed by MTBE (20 mL×2). After drying, 2-formyl-4-methylphenyl 2-oxooxazolidine-3-carboxylate (13.3 g) was obtained as a white solid. Yield: 73%. 1H NMR (Acetone-d6, 300 MHz): δ=10.25 (s, 1H), 7.78 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 4.58 (t, J=7.8 Hz, 2H), 4.32 (t, J=7.5 Hz, 2H), 2.47 (s, 3H).

Provenance & Evidence