反应详情

To a solution of 2-(2-methylquinolin-8-yl)acetic acid (1.45 g, 7.21 mmol) in dry MeOH (100 mL) was added chlorotrimethylsilane (1.82 mL, 14.4 mmol) dropwise at 0° C. After addition, the reaction mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (20 mL). The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give methyl 2-(2-methylquinolin-8-yl)acetate (1.35 g, 87.0%) as an oil.

1. additionAfter addition
2. temperatureat reflux for 2 hours
3. customthe solvent was removed under reduced pressure
4. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate (20 mL)
5. customThe organic layer was separated
6. washwashed with brine
7. dry with materialdried (sodium sulfate)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)