Реакция #155322

Уравнение реакции

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

Выход 42.0%

Растворители

ethyl acetate

Water

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 62 hours
2. 2
   Другоеthe resulting mixture was subjected to separation
3. 3
   ПромывкаThe thus-obtained organic layer was washed with water
4. 4
   Сушкаdried over anhydrous sodium sulfate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue was purified
7. 7
   КонцентрированиеThe purified product was concentrated under reduced pressure
8. 8
   Другоеto recrystallize the residue from ethyl acetate-n-hexane

Методика

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%).

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