Reacción #2267079

Ecuación de reacción

14

6-Acetylamino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

sodium hydroxide

HCl

→

22

6-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Disolventes

DMSO

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate three times
2. 2
   LavadoThe combined organic phase was washed with water
3. 3
   Secadodried over Na2SO4
4. 4
   OtroRemoval of the solvent

Procedimiento

A solution of 14 (1.8 g) in 5 ml of DMSO and 30 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried over Na2SO4. Removal of the solvent afforded 22 (1.9 g) as a syrup, which was used directly for the next step.

Fuente