反应详情

温度

-78 °C

To a stirring solution of 2-(3-bromo-phenyl)-5-methyl-thiophene (0.395 mmol) in tetrahydrofuran (4 mL) at −78° C. was slowly added a 2M solution of n-butyllithium in cyclohexane (0.435 mmol, 1.1 eq.). The resulting solution was stirred 30 min at −78° C. and solid [8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde (0.395 mmol) was added. Stirring at −78° C. was continued for 10 min and the reaction was allowed to warm to room temperature and was stirred 1 h. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give a yellow oil that was purified by column chromatography using 20% ethyl acetate/hexanes to give the final product as a light yellow solid (0.18 mmol, 46%). MS (ESI) m/z 486.4.

1. stirringStirring at −78° C.
2. waitwas continued for 10 min
3. temperatureto warm to room temperature
4. stirringwas stirred 1 h
5. customThe reaction mixture was then quenched with saturated aqueous ammonium chloride solution (10 mL)
6. extractionextracted with ethyl acetate (3×10 mL)
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a yellow oil that
11. customwas purified by column chromatography