Reacción #45555

Ecuación de reacción

p-toluenesulfonic acid monohydrate

N-(3-bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

sodium bicarbonate water

→

compound

Rendimiento 84.3%

7-Bromo-2-tert-butyl-5-methyl-6-styryl-1,3-benzoxazole-4-carbonitrile

Rendimiento 84.3%

Disolventes

Toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby refluxing with a Dean-Stark condenser for 2.5 hours
2. 2
   TemperaturaAfter cooling
3. 3
   Extracciónthe product was extracted with ethyl acetate (30 ml×2)
4. 4
   LavadoThe organic layer was washed with saturated brine (30 ml)
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otrothe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1)

Procedimiento

Toluene (3 ml), p-toluenesulfonic acid monohydrate (1.4 mg, 7.5 μmol) were added to N-(3-bromo-6-cyano-2-hydroxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide (I-14) (31 mg, 75 μmol), followed by refluxing with a Dean-Stark condenser for 2.5 hours. After cooling, saturated sodium bicarbonate water (30 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (30 ml×2). The organic layer was washed with saturated brine (30 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1) to obtain the entitled compound (25 mg, 84%) as a colorless solid.

Fuente