反应详情

A slurry of (7-methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-acetic acid methyl ester (5.0 g, 20 mmol) in tetrahydrofuran (40 mL) was treated with potassium bis(trimethylsilyl)amide (0.5 M in toluene, 41 mL, 21 mmol) at 25° C. and the mixture heated to reflux. After 1 h at reflux, ethyl iodide (16 mL, 200 mmol) was added. After an additional 3 h at reflux, the cooled mixture was quenched with 0.1N aqueous HCl (50 mL) and concentrated in vacuo. Water (200 mL) was added and the aqueous phase extracted with chloroform (3×200 mL). The extracts were dried (K2CO3) and concentrated in vacuo to give the crude product (5.3 g). Flash chromatography (225 g silica; 2:1, then 1:1 hexane-ether, then 100% ether) gave the title compound (4.4 g, 79% yield) as a white solid.

1. temperaturethe mixture heated to reflux
2. temperatureAfter 1 h at reflux
3. temperatureAfter an additional 3 h at reflux
4. customthe cooled mixture was quenched with 0.1N aqueous HCl (50 mL)
5. concentrationconcentrated in vacuo
6. additionWater (200 mL) was added
7. extractionthe aqueous phase extracted with chloroform (3×200 mL)
8. dry with materialThe extracts were dried (K2CO3)
9. concentrationconcentrated in vacuo
10. customto give the crude product (5.3 g)