反应详情

温度

50 °C

To a solution of methyl 2-hydroxynicotinate (300 mg) in dimethylformamide (3 ml), 0.42 ml of bromocyclopropane and 542 mg of potassium carbonate were added, and the reaction solution was stirred overnight at 50° C. The reaction solution was cooled, then diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of lithium aluminum hydride (143 mg) in tetrahydrofuran (2 ml), a solution of the crude product in tetrahydrofuran 3 ml was added under ice-cooling. The reaction solution was stirred at the same temperature for 1 hour, followed by adding sodium sulfate decahydrate and further stirring the mixture at the same temperature for 1 hour. The reaction solution was Celite-filtered, the filtrate was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50:50)) to afford the title compound as a colorless oil.

1. temperatureThe reaction solution was cooled
2. extractionextracted with ethyl acetate
3. washThe combined organic layers were washed with a saturated saline solution
4. dry with materialdried over anhydrous sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customto afford a crude product as a yellow oil
7. temperaturecooling
8. stirringThe reaction solution was stirred at the same temperature for 1 hour
9. stirringfurther stirring the mixture at the same temperature for 1 hour
10. filtrationThe reaction solution was Celite-filtered
11. distillationthe filtrate was distilled off under reduced pressure
12. customthe residue obtained
13. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (95:5-50:50))