Réaction #67967

Équation de réaction

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

Solvants

ethyl acetate

water

Conditions de réaction

Traitement

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
   TempératureThe reaction mixture was cooled to room temperature
6. 6
   AutreThe organic layer was separated
7. 7
   Extractionthe aqueous layer was extracted twice with ethyl acetate
8. 8
   Lavagethe resultant solution was washed with a saturated sodium chloride solution
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    Autrethe solvent was removed under reduced pressure
11. 11
    Autrethe residue thus obtained
12. 12
    Autrewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1]

Mode opératoire

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.

Source