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0 °C

A mixture of (E)-4-(4-fluorobenzylideneamino)isobenzofuran-1(3H)-one (510 mg, 2 mmol) and 4,5-dimethyl-4H-1,2,4-triazole-3-carbaldehyde (275 mg, 2.2 mmol) in ethyl propionate (20 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (184 mg, 8 mmol) in ethanol (10 mL)) was added dropwise. After the addition, the mixture was stirred at 10° C. for 2 hr, then 30° C. for 4 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (30 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give a crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1 then ethyl acetate/methanol=30:1) to afford the title compound (170 mg, yield: 21%). LC-MS (ESI) m/z: 409 (M+1)+.

1. additionAfter the addition
2. wait30° C. for 4 hr
3. customThe mixture was quenched with water (10 mL) and solvent
4. customwas removed in vacuum
5. dissolutionThe residue was dissolved in water
6. extractionextracted with ethyl acetate (30 mL×4)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. customto give a crude product
11. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=3:1