反应详情

温度

-78 °C

To a stirring solution of [8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde (0.380 mmol) in tetrahydrofuran (4 mL) at −78° C. was dropwise added a 1M solution of 3,4-(methylenedioxy)phenylmagnesium bromide in 1:1 toluene/tetrahydrofuran (0.380 mmol, 1.0 eq.) and stirring at −78° C. was continued for 10 min. The reaction mixture was then allowed to warm to room temperature and was stirred 1 h then quenched with saturated aqueous sodium bicarbonate solution (2 mL). After stirring 15 min the reaction mixture was extracted with ethyl acetate (3×5 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to give a brown oil that was purified by column chromatography using 30% ethyl acetate/hexanes to give the final product as a white foam (0.126 mmol, 33%). MS (ESI) m/z 434.2; HRMS: calcd for C25H20ClNO4+H+, 434.11536; found (ESI, [M+H]+ Obs'd), 434.1150.

1. temperatureto warm to room temperature
2. stirringwas stirred 1 h
3. customthen quenched with saturated aqueous sodium bicarbonate solution (2 mL)
4. stirringAfter stirring 15 min the reaction mixture
5. extractionwas extracted with ethyl acetate (3×5 mL)
6. dry with materialthe combined organic layers were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a brown oil that
10. customwas purified by column chromatography