Reaktion #7827

Reaktionsgleichung

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

p-toluenesulfonic acid monohydrate

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed overnight
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigereaction to rt
4. 4
   Filtrationfiltered
5. 5
   Waschenwashing with warm chloroform and concentrated filtrate in vacuo
6. 6
   SonstigeThe resulting brown oil was purified by flash chromatography on silica gel using 1:4 EtOAc

Vorschrift

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.

Quelle