反应详情

温度

-40 °C

To a THF (20 ml) solution of methyl quinoline-6-carboxylate (984 mg, 5.26 mmol, J. O. C., 2002, 67, 7890) was added t-butylmagnesium chloride in THF (15.8 ml, 1M solution) dropwise at −78° C. over 30 min. The mixture was stirred at −78° C. for 30 minutes and at −40° C. for 30 minutes, then at room temperature for 1 hour. The reaction was quenched with saturated ammonium chloride aqueous solution (100 ml) and extracted with EtOAc (100 ml×2) which was dried over sodium sulfate. Then, filtration, evaporation gave yellow oil, which was solved in THF (50 ml) and manganese dioxide (1.83 g 15.8 mmol) was added there. After the mixture was stirred at room temperature for 2.5 hours, the precipitate was removed through a pad of Celite and washed with EtOAc. The filtrate was concentrated and purified through silica gel column chromatography eluting with Hexane/EtOAc (20:1) to furnish the title compound (348 mg, 27% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (9H, s), 3.99 (3H, s), 7.59 (1H, d, J=8.8 Hz), 8.08 (1H, d, J=8.8 Hz), 8.17 (1H, d, J=8.8 Hz), 8.26 (1H, dd, J=2.2, 8.8 Hz), 8.55 (1H, d, J=2.2 Hz) MS (ESI): m/z 244 (M+H)+.

1. waitat room temperature for 1 hour
2. customThe reaction was quenched with saturated ammonium chloride aqueous solution (100 ml)
3. extractionextracted with EtOAc (100 ml×2) which
4. dry with materialwas dried over sodium sulfate
5. filtrationThen, filtration, evaporation
6. customgave yellow oil, which
7. stirringAfter the mixture was stirred at room temperature for 2.5 hours
8. customthe precipitate was removed through a pad of Celite
9. washwashed with EtOAc
10. concentrationThe filtrate was concentrated
11. custompurified through silica gel column chromatography
12. washeluting with Hexane/EtOAc (20:1)