Reacción #7827

Ecuación de reacción

N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide

p-toluenesulfonic acid monohydrate

→

2-(3-methoxy-4-methylphenyl)-1,3-benzoxazole

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed overnight
2. 2
   TemperaturaAfter cooling
3. 3
   Otroreaction to rt
4. 4
   Filtraciónfiltered
5. 5
   Lavadowashing with warm chloroform and concentrated filtrate in vacuo
6. 6
   OtroThe resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc

Procedimiento

A mixture of N-(2-hydroxyphenyl)-3-methoxy-4-methylbenzamide (1.5 g, 5.8 mmol), toluene (30 mL), p-toluenesulfonic acid monohydrate (7.6 g, 40 mmol) and molecular sieves was refluxed overnight. After cooling reaction to rt, filtered washing with warm chloroform and concentrated filtrate in vacuo. The resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc:hexanes to give the desired intermediate, 2-(3-methoxy-4-methylphenyl)-1,3-benzoxazole, as a colorless solid.

Fuente