Reacción #318757

Ecuación de reacción

ethylene oxide

4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

→

2-(2-Hydroxyethyl)-4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   OtroWater was removed under reduced pressure
3. 3
   Otrothe residue flash chromatographed over silica gel
4. 4
   LavadoElution with 2% isopropanol-98% CH2Cl2
5. 5
   Otrogave product which
6. 6
   Otrowas recrystallized from EtOAc-hexane
7. 7
   Otroto give the 2-hydroxethyl derivative (0.39 g, 16%), m.p. 140-1°

Procedimiento

To approximately 2 ml of ethylene oxide cooled in an ice bath was added a suspension of 4-nitro-2H-1,2-benzisothiazol-3-one 1,1-dioxide (2.0 g, 8.76 mmol) in H2O (140 ml). After stirring in the ice bath for 1 hour, the mixture was allowed to stir at 20-25° for 18 hours. Water was removed under reduced pressure and the residue flash chromatographed over silica gel. Elution with 2% isopropanol-98% CH2Cl2 gave product which was recrystallized from EtOAc-hexane to give the 2-hydroxethyl derivative (0.39 g, 16%), m.p. 140-1°.

Fuente