Реакция #68012

Уравнение реакции

8-methylquinolin-2(1H)-one

sodium hydride

hydrochloric acid

2-bromomethyl-1,3-dioxolane

→

1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one

Растворители

N,N-dimethylformamide

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added under a nitrogen atmosphere
2. 2
   workup.STIRRINGthe mixture was stirred at 90° C. for 48 hours
3. 3
   ТемператураThe reaction mixture was cooled to room temperature
4. 4
   ДругоеThe organic layer was separated
5. 5
   Экстракцияthe aqueous layer was extracted with ethyl acetate
6. 6
   Промывкаthe resultant solution was washed with an aqueous saturated sodium chloride solution
7. 7
   Сушкаdried over anhydrous magnesium sulfate
8. 8
   Другоеthe solvent was removed under reduced pressure
9. 9
   ДругоеThe residue thus obtained
10. 10
    Другоеwas purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=8:1]

Методика

To 3 mL of an N,N-dimethylformamide solution containing 0.17 g of 8-methylquinolin-2(1H)-one, 0.13 g of 60% sodium hydride was added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. Thereto was added 0.89 g of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90° C. for 48 hours. The reaction mixture was cooled to room temperature, then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Chromatorex-NH, manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=8:1] to obtain 0.18 g of a pale yellow oily substance, 1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one.

Источник