Reaktion #67967

Reaktionsgleichung

2-bromomethyl-1,3-dioxolane

N,N-dimethylformamide

quinolin-2(1H)-one

sodium hydride

sodium hydride

2-bromomethyl-1,3-dioxolane

sodium hydride

2-bromomethyl-1,3-dioxolane

→

1-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one

Lösungsmittel

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe reaction mixture was stirred at 85 to 95° C. for 30 minutes
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   workup.STIRRINGstirred for 1 hour and 30 minutes
5. 5
   TemperaturThe reaction mixture was cooled to room temperature
6. 6
   SonstigeThe organic layer was separated
7. 7
   Extraktionthe aqueous layer was extracted twice with ethyl acetate
8. 8
   Waschenthe resultant solution was washed with a saturated sodium chloride solution
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was removed under reduced pressure
11. 11
    Sonstigethe residue thus obtained
12. 12
    Sonstigewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1]

Vorschrift

To 11.5 mL of an N,N-dimethylformamide solution containing 1.15 g of quinolin-2(1H)-one, 0.35 g of 60% sodium hydride was added, and the mixture was stirred at 50 to 55° C. for 20 minutes. Thereto was added 0.90 mL of 2-bromomethyl-1,3-dioxolane, and the reaction mixture was stirred at 85 to 95° C. for 30 minutes. The reaction mixture was further added with 0.35 g of 60% sodium hydride and 0.90 mL of 2-bromomethyl-1,3-dioxolane, and stirred for 1 hour. The mixture was further added with 0.35 g of 60% sodium hydride and 0.90 mL of 2-bromomethyl-1,3-dioxolane, and stirred for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1] to obtain 0.89 g of a yellow oily substance, 1-(1,3-dioxolan-2-ylmethyl)quinolin-2(1H)-one.

Quelle