反応 #68012

反応方程式

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

溶媒

N,N-dimethylformamide

ethyl acetate

反応条件

後処理

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

実験手順

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.

出典