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温度

0 °C

A mixture of (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (237 mg, 1 mmol) and 4,5-dimethyl-4H-1,2,4-triazole-3-carbaldehyde (150 mg, 1.2 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol [sodium (92 mg, 4 mmol) in ethanol (5 mL)] was added dropwise. After the addition, the mixture was stirred at 10° C. for 5 hr, then 30° C. 2.5 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 crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1 then ethyl acetate/methanol=15:1) to give the title compound (60 mg, yield: 15%). LC-MS (ESI) m/z: 391 (M+1)+.

1. additionAfter the addition
2. custom30° C
3. custom2.5 hr
4. customThe mixture was quenched with water (10 mL) and solvent
5. customwas removed in vacuum
6. dissolutionThe residue was dissolved in water
7. extractionextracted with ethyl acetate (30 mL×4)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customto give crude product
12. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=5:1