反应详情

温度

25 °C

A mixture of 5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone (10.0 g), lithium hydride (0.78 g), and dimethylformamide (400 ml) was stirred for 3 hrs at 25° C., under nitrogen. 1-Bromohexane (10.6 g) was added and the mixture was stirred for an additional eighteen hrs. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue as purified by high performance liquid chromatography (silica gel, two columns, eluted with 50% ethyl acetate/hexane). The appropriate fractions were collected and evaporated to give 4.6 (31%) of 1-hexyl-5,6,7,8-tetrahydro-5-oxo-2(1H)-quinolinone.

1. stirringthe mixture was stirred for an additional eighteen hrs
2. concentrationThe reaction mixture was concentrated
3. customthe residue was partitioned between ethyl acetate and water
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate
6. washThe combined organic extracts were washed with water and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated
10. customThe residue as purified by high performance liquid chromatography (silica gel, two columns, eluted with 50% ethyl acetate/hexane)
11. customThe appropriate fractions were collected
12. customevaporated