Réaction #68033

Équation de réaction

4-acetyl-3,4-dihydro-2-oxo-1H-quinoxaline

sodium hydride

hydrochloric acid

2-bromomethyl-1,3-dioxolane

→

4-acetyl-1-(1,3-dioxolan-2-ylmethyl)-2-oxo-3,4-dihydro-1H-quinoxaline

Solvants

N,N-dimethylformamide

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe mixture was stirred at 90° C. for 6 hours
3. 3
   TempératureThe reaction mixture was cooled to room temperature
4. 4
   AutreThe organic layer was separated
5. 5
   Lavagewashed sequentially with water
6. 6
   Séchagean aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
7. 7
   Autrethe solvent was removed under reduced pressure
8. 8
   AutreThe residue thus obtained
9. 9
   Autrewas purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform]

Mode opératoire

To 15 mL of an N,N-dimethylformamide solution containing 957 mg of 4-acetyl-3,4-dihydro-2-oxo-1H-quinoxaline, 668 mg of sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Thereto was added 2.6 mL of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90° C. for 6 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, washed sequentially with water and 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; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform] to obtain 1.30 g of a brown oily substance, 4-acetyl-1-(1,3-dioxolan-2-ylmethyl)-2-oxo-3,4-dihydro-1H-quinoxaline.

Source