Reacción #155309

Ecuación de reacción

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

1-iodopropane

potassium carbonate

→

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

Rendimiento 96.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile heating
2. 2
   Temperaturaunder reflux
3. 3
   Concentraciónconcentrated to dryness under reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Extracciónfollowed by extraction
6. 6
   ConcentraciónThe thus-obtained organic layer was concentrated to dryness under reduced pressure
7. 7
   Otrothe residue was then purified
8. 8
   ConcentraciónThe purified product was concentrated to dryness under reduced pressure

Procedimiento

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%).

Fuente