Reaktion #155309

Reaktionsgleichung

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

1-iodopropane

potassium carbonate

→

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

Ausbeute 96.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile heating
2. 2
   Temperaturunder reflux
3. 3
   Einengenconcentrated to dryness under reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Extraktionfollowed by extraction
6. 6
   EinengenThe thus-obtained organic layer was concentrated to dryness under reduced pressure
7. 7
   Sonstigethe residue was then purified
8. 8
   EinengenThe purified product was concentrated to dryness under reduced pressure

Vorschrift

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%).

Quelle