反应详情

温度

0 °C

A stirred solution of di-tert-butyl malonate (1.5 mL, 6.70 mmol) in N,N-dimethylformamide (15 mL) at 0° C. under argon was treated portionwise over 10 minutes with sodium hydride (276 mg of 60% oil dispersion, 6.90 mmol) and stirred at 0° C. for 15 minutes before allowing to warm to room temperature over 1 hour. A white precipitate was produced. The stirred mixture was cooled to 0° C. and treated with a solution of 4-fluoro-3-nitrotoluene (1.0 g, 6.45 mmol) in N,N-dimethylformamide (2 mL) and a deep purple colour was immediately formed. This mixture was stirred at room temperature for 28 hours then heated at 70° C. for 6 hours. The mixture was cooled, then diluted with water (100 mL) and extracted with Et2O (2×50 mL). The combined extract was washed with water (70 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography on silica gel (40 g) eluting with toluene to afford the title compound as a yellow oil (660 mg, 29%).

1. temperatureto warm to room temperature over 1 hour
2. customA white precipitate was produced
3. temperatureThe stirred mixture was cooled to 0° C.
4. customa deep purple colour was immediately formed
5. stirringThis mixture was stirred at room temperature for 28 hours
6. temperaturethen heated at 70° C. for 6 hours
7. temperatureThe mixture was cooled
8. extractionextracted with Et2O (2×50 mL)
9. extractionThe combined extract
10. washwas washed with water (70 mL)
11. dry with materialdried (Na2SO4)
12. concentrationconcentrated under vacuum
13. customThe residue was purified by chromatography on silica gel (40 g)
14. washeluting with toluene