反应详情

温度

-78 °C

n-Butyllithium in hexanes (12.7 mL, 1.6 M, 20.3 mmol) was added dropwise to a solution of (2-(2-bromothiophen-3-yl)ethoxy)(tert-butyl)dimethylsilane (5.9 g, 18.4 mmol) in anhydrous THF (15 mL) at −78° C. The resulting mixture was stirred at −78° C. for 30 min and 4-fluorobenzaldehyde (2.5 g, 20.3 mmol) in THF was added slowly. The mixture was stirred at −78° C. for 2 h and then warmed up to rt. After cooling again to 0° C. 50 mL of aqueous saturated ammonium chloride was added and the mixture was extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the product was purified by flash chromatography eluting with ethyl acetate/hexane (1:3) to afford the title compound as a solid (3.8 g, 59%).

1. stirringThe mixture was stirred at −78° C. for 2 h
2. temperaturewarmed up to rt
3. temperatureAfter cooling again to 0° C
4. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
5. washThe combined organic layers were washed with brine (100 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customThe solvent was evaporated in vacuo
9. customthe product was purified by flash chromatography
10. washeluting with ethyl acetate/hexane (1:3)