반응 #155322

반응 방정식

Methyl iodide

DMF

2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one

sodium hydride

→

2-furan-3-yl-4-methyl-5-propoxy-4H-benzo[f]quinolin-1-one

수율 42.0%

용매

ethyl acetate

Water

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 62 hours
2. 2
   기타the resulting mixture was subjected to separation
3. 3
   세척The thus-obtained organic layer was washed with water
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified
7. 7
   농축The purified product was concentrated under reduced pressure
8. 8
   기타to recrystallize the residue from ethyl acetate-n-hexane

실험 절차

To a DMF solution (5 ml) of 2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one (300 mg, 0.94 mmol) was added sodium hydride (60% oil base, 61 mg, 1.4 mmol), and then the mixture was stirred at room temperature for 5 minutes. Methyl iodide (181 mg, 1.27 mmol) was added thereto and the resulting mixture was stirred at room temperature for 62 hours. Water and ethyl acetate were added to the reaction mixture and the resulting mixture was subjected to separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=90:1→80:1). The purified product was concentrated under reduced pressure to recrystallize the residue from ethyl acetate-n-hexane, giving a pale gray powder of 2-furan-3-yl-4-methyl-5-propoxy-4H-benzo[f]quinolin-1-one (130 mg, yield: 42%).

출처