反応 #155309

反応方程式

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

1-iodopropane

potassium carbonate

→

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

収率 96.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度while heating
2. 2
   温度under reflux
3. 3
   濃縮concentrated to dryness under reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   抽出followed by extraction
6. 6
   濃縮The thus-obtained organic layer was concentrated to dryness under reduced pressure
7. 7
   その他the residue was then purified
8. 8
   濃縮The purified product was concentrated to dryness under reduced pressure

実験手順

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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