반응 #68012

반응 방정식

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

용매

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

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

실험 절차

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.

출처