Реакция #155309

Уравнение реакции

N-(3-Hydroxynaphthalen-2-yl)acetamide

1-iodopropane

potassium carbonate

→

N-(3-propoxynaphthalen-2-yl)acetamide

Выход 96.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Температураwhile heating
2. 2
   Температураunder reflux
3. 3
   Концентрированиеconcentrated to dryness under reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Экстракцияfollowed by extraction
6. 6
   КонцентрированиеThe thus-obtained organic layer was concentrated to dryness under reduced pressure
7. 7
   Другоеthe residue was then purified
8. 8
   КонцентрированиеThe purified product was concentrated to dryness under reduced pressure

Методика

N-(3-Hydroxynaphthalen-2-yl)acetamide (4.87 g, 24.2 mmol) was suspended in acetonitrile (50 ml). A 1-iodopropane (4.52 g, 26.6 mmol) acetonitrile solution (40 ml) and potassium carbonate (4.35 g, 31.5 mmol) were added thereto, and the resulting mixture was stirred for 3 hours while heating under reflux. The mixture was then cooled to room temperature and concentrated to dryness under reduced pressure. Water was added to the residue, followed by extraction using dichloromethane. The thus-obtained organic layer was concentrated to dryness under reduced pressure, and the residue was then purified using silica gel column chromatography (dichloromethane:ethyl acetate=20:1). The purified product was concentrated to dryness under reduced pressure, giving a white powder of N-(3-propoxynaphthalen-2-yl)acetamide (5.64 g, yield: 96%).

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