Reacción #3870

Ecuación de reacción

7-Methoxy-3-piperidino-2,2-dimethylbenzofuran

HBr

→

desired product

7-Hydroxy-3-piperidino-2,2-dimethylbenzofuran

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution refluxed for 3 hours
2. 2
   workup.ADDITIONThe reaction mixture is poured
3. 3
   OtroThe alkaline reaction mixture
4. 4
   Extracciónis extracted with methylene chloride
5. 5
   Lavadothe organic phase washed with water
6. 6
   Otrodried
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo
9. 9
   OtroThe residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3)

Procedimiento

7-Methoxy-3-piperidino-2,2-dimethylbenzofuran (65.1 g) is added to a stirred mixture of glacial acetic acid (340 ml) and 48% HBr (340 ml) and the solution refluxed for 3 hours. The reaction mixture is poured into crushed ice/H2O and brought to a pH=8-10. The alkaline reaction mixture is extracted with methylene chloride and the organic phase washed with water, dried, filtered and evaporated in vacuo. The residue is chromatographed on silica gel eluting with ethyl acetate/hexane (1:3) affording the desired product as a liquid.

Fuente