تفاعل #68012

معادلة التفاعل

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

المذيبات

N,N-dimethylformamide

ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر