Reacción #5380

Ecuación de reacción

2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole

octyl iodide

potassium hydroxide

butanol

→

2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole

Rendimiento 56.6%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby refluxing for 310 minutes
2. 2
   Extracciónextracted from ethyl acetate
3. 3
   Otroto obtain an organic layer
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried with mirabilite
6. 6
   Otrodried under reduced pressure
7. 7
   Otroto obtain a resultant
8. 8
   OtroThe resultant was recrystallized from ethylacetate
9. 9
   Otroto obtain a crystal
10. 10
    FiltraciónThe crystal was filtered
11. 11
    Otropurified by silica gel column chromatography (eluent: toluene)
12. 12
    Otrorecrystallized from acetone

Procedimiento

In a 30ml round-bottom flask, 0.47 g (1.48 m mole) of 2-(6-hydroxy-2-naphthyl)-5-butylbenzooxazole, 0.43 g (1.79 m mole) of octyl iodide, 0.12 g (1.82 m mole) of potassium hydroxide and 5 ml of butanol were placed, followed by refluxing for 310 minutes. The reaction mixture was poured into water, extracted from ethyl acetate to obtain an organic layer. The organic layer was washed with water dried with mirabilite and dried under reduced pressure to obtain a resultant. The resultant was recrystallized from ethylacetate to obtain a crystal. The crystal was filtered, purified by silica gel column chromatography (eluent: toluene) and recrystallized from acetone to obtain 0.36 g of 2-(6-octyloxy-2-naphthyl)-5-butylbenzooxazole (Yield: 56.6%). ##STR190##

Fuente