反应详情

温度

120 °C

To a solution of pyrimidin-5-ol (500 mg, 5.20 mmol) in DMF (5.20 mL) under argon was added 4-fluorobenzaldehyde (0.558 mL, 5.20 mmol), sodium methanesulfinate (133 mg, 1.30 mmol), and potassium carbonate (1.079 g, 7.81 mmol). The reaction mixture was heated at 120° C. for 3 hour. The mixture was allowed to cool to room temperature and was diluted with water (25 mL). The mixture was extracted with EtOAc (2×25 mL). The combined organic layers were washed with brine (2×50 mL), dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate], providing 4-(pyrimidin-5-yloxy)benzaldehyde (666 mg) as a yellow solid. LCMS m/z 201.0 (M+H)+, Rt 0.52 min.

1. temperatureto cool to room temperature
2. extractionThe mixture was extracted with EtOAc (2×25 mL)
3. washThe combined organic layers were washed with brine (2×50 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered off
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography [SiO2, 24 g, heptane/ethyl acetate]