Reaktion #67987

Reaktionsgleichung

sodium hydride

7-methoxy-4-methylquinolin-2(1H)-one

sodium hydride

potassium carbonate

2-(8-cyano-1,4-dioxaspiro[4.5]decan-8-yl)ethyl methanesulfonate

→

8-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 50 to 55° C. for 2 hours and 50 minutes
2. 2
   workup.STIRRINGafter further stirring for 3 hours
3. 3
   workup.STIRRINGfurther stirred for 3 hours
4. 4
   SonstigeThe organic layer was separated
5. 5
   Extraktionthe aqueous layer was extracted with ethyl acetate
6. 6
   Waschenthe resultant solution was washed with an aqueous saturated sodium chloride solution
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   Sonstigethe solvent was removed under reduced pressure
9. 9
   SonstigeThe residue thus obtained
10. 10
    Sonstigewas purified by flash silica gel column chromatography [hexane: gradient elution of ethyl acetate 30:70]

Vorschrift

To 10 mL of an N,N-dimethylformamide suspension containing 0.63 g of 7-methoxy-4-methylquinolin-2(1H)-one, 0.17 g of 60% sodium hydride at 55° C., and the mixture was stirred at the same temperature for 35 minutes. Thereto was added dropwise 8 mL of an N,N-dimethylformamide solution containing 0.99 g of 2-(8-cyano-1,4-dioxaspiro[4.5]decan-8-yl)ethyl methanesulfonate at 50° C., and the mixture was stirred at 50 to 55° C. for 2 hours and 50 minutes. Thereto was added 53 mg of 60% sodium hydride at the same temperature, and after further stirring for 3 hours, the mixture was added with 0.46 g of potassium carbonate at the same temperature, and further stirred for 3 hours. 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 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 flash silica gel column chromatography [hexane: gradient elution of ethyl acetate 30:70] to obtain 200 mg g of a white solid, 8-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile.

Quelle