反应详情

温度

-78 °C

3-Butenylmagnesium bromide (0.5 M in THF, 100 mL, 50.0 mmol, 1.7 equiv) was added was added to a solution of 4-methoxyquinoline (4.65 g, 29.2 mmol, 1 equiv) in tetrahydrofuran (195 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, then benzyl chloroformate (8.34 mL, 58.4 mmol, 2.00 equiv) was added via syringe over 5 min. Stirred for an additional 15 minutes at −78° C., then the cooling bath was removed and the reaction mixture was allowed to warm to 23° C. After 1 h, methanol was added (20 mL). After stirring for 5 min, aqueous hydrochloric acid solution (2 N, 20 mL) was added and the mixture was stirred for 10 min. The mixture was then concentrated by rotary evaporation to remove most of the tetrahydrofuran and methanol, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (5% ethyl acetate-hexanes, grading to 20% ethyl acetate-hexanes) to afford 28A as a colorless oil. [M+H]+: 336.2.

1. stirringStirred for an additional 15 minutes at −78° C.
2. customthe cooling bath was removed
3. temperatureto warm to 23° C
4. waitAfter 1 h
5. additionmethanol was added (20 mL)
6. stirringAfter stirring for 5 min
7. additionaqueous hydrochloric acid solution (2 N, 20 mL) was added
8. stirringthe mixture was stirred for 10 min
9. concentrationThe mixture was then concentrated by rotary evaporation
10. customto remove most of the tetrahydrofuran and methanol
11. customthe residue was partitioned between ethyl acetate and water
12. washThe organic phase was washed with brine
13. dry with materialthe washed solution was dried over sodium sulfate
14. filtrationThe dried solution was filtered
15. concentrationthe filtrate was concentrated
16. customThe residue was purified by flash-column chromatography (5% ethyl acetate-hexanes, grading to 20% ethyl acetate-hexanes)