反应详情

To a solution of 7-methylquinoline (1.63 g, 11.4 mmol) in dry THF (10 mL), cooled by ice/water, was added phenyllithium (1.9 M in cyclohexane/ether 70/30, 6.0 mL, 11.4 mmol) dropwise over 5 min. After 15 min, the cooling bath was removed, and the solution was stirred at ambient temperature for 5 h. The reaction was quenched by adding MeOH, and stirring was continued overnight. Water was added, the mixture was extracted with EtOAc (3×35 mL), and the combined extracts were dried over MgSO4. The drying agent was filtered off, and air was bubbled into the solution for 7 d. The solvent was evaporated; the residue was dissolved in warm (≈50° C.) EtOAc/hexanes and filtered warm. The filtrate was concentrated and dried in vacuo, giving the crude title compound that was used directly for the next step. A sample was purified further by chromatography on silica gel (Jones Flashmaster, eluting with hexanes:EtOAc 3:1→2:1→1:1). 1H NMR (CDCl3, 400 MHz): δ=2.58 (s, 3H), 7.31 (d, J=3.7 Hz, 1H), 7.36-7.49 (m, 1H), 7.52 (t, J=8.0 Hz, 2H), 7.72 (d, J=8.2 Hz, 1H), 7.82 (d, J=8.2 Hz, 1H), 7.96 (s, 1H), 8.16 (t, J=8.0 Hz, 2H). MS (ES+): m/z 220.3 (100) [MH+]. HPLC: tR=2.7 min (Platform II, nonpolar—5 min).

1. customthe cooling bath was removed
2. customThe reaction was quenched
3. additionby adding MeOH
4. stirringstirring
5. waitwas continued overnight
6. additionWater was added
7. extractionthe mixture was extracted with EtOAc (3×35 mL)
8. dry with materialthe combined extracts were dried over MgSO4
9. filtrationThe drying agent was filtered off
10. customair was bubbled into the solution for 7 d
11. customThe solvent was evaporated
12. dissolutionthe residue was dissolved
13. temperaturein warm (≈50° C.) EtOAc/hexanes
14. filtrationfiltered
15. temperaturewarm
16. concentrationThe filtrate was concentrated
17. customdried in vacuo