Réaction #67964

Équation de réaction

sodium hydrogen carbonate

2-bromomethyl-1,3-dioxolane

7-methylquinolin-2(1H)-one

cesium carbonate

→

1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one

Solvants

water

ethyl acetate

dimethyl sulfoxide

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   AutreThe organic layer was separated
3. 3
   Extractionthe aqueous layer was extracted with ethyl acetate
4. 4
   Lavagethe resultant solution was washed with water
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Autrethe solvent was removed under reduced pressure
7. 7
   AutreThe residue thus obtained
8. 8
   Autrewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

Mode opératoire

To 6.3 mL of a dimethyl sulfoxide solution containing 1.1 g of 2-bromomethyl-1,3-dioxolane, 1.0 g of 7-methylquinolin-2(1H)-one and 3.1 g of cesium carbonate were added, and the mixture was stirred at 60 to 70° C. for 1 hour. The reaction mixture was added with ethyl acetate, water and an aqueous saturated sodium hydrogen carbonate solution. 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 water 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 [eluent; hexane:ethyl acetate=2:3] to obtain 0.60 g of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one.

Source