反应详情

Magnesium chloride (27.7 g, 0.29 mol) was added to 2-methoxyethanol (400 mL) and the mixture heated to reflux. A solution of 3-(3,4-Dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester (0.29 mol) in 2-methoxyethanol (100 mL) and tetrahydrofuran (40 mL) was slowly added to the MgCl2 mixture over 1 hour. Upon completion of addition, the mixture was stirred for 5 hours at reflux, and then concentrated in vacuo. The concentrated crude mixture was treated with 2N hydrochloric acid (500 mL) and extracted with dichloromethane (3×400 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography, eluting with 20% ethyl acetate/hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 31.6 g (48%) of the desired compound as an orange solid.

1. temperaturethe mixture heated to reflux
2. additionUpon completion of addition
3. temperatureat reflux
4. concentrationconcentrated in vacuo
5. concentrationThe concentrated crude mixture
6. additionwas treated with 2N hydrochloric acid (500 mL)
7. extractionextracted with dichloromethane (3×400 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. washeluting with 20% ethyl acetate/hexanes
12. additionFractions containing product
13. concentrationconcentrated under reduced pressure