Reacción #67267

Ecuación de reacción

5-bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate

KOH

→

crude title compound

Rendimiento 57.9%

[(2R)-7-BROMO-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHANOL

Rendimiento 57.9%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónwas then concentrated
2. 2
   workup.ADDITIONWater was added
3. 3
   workup.ADDITIONAqueous HCl (1 N) was added
4. 4
   Extracciónthe solution was then extracted with EtOAc (3×75 ml)
5. 5
   LavadoThe combined organic phases were washed with brine
6. 6
   Secadodried (Na2SO4)
7. 7
   Otroevaporated to dryness
8. 8
   OtroPurification on flash column chromatography (isooctane/EtOAc)

Procedimiento

5-bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate (8.5 g, 31 mmol) was dissolved in dioxane. At 0° C., KOH (10%) was added. The mixture was stirred in rt for 1 h and 30 min and was then concentrated. Water was added. Aqueous HCl (1 N) was added to neutralize and the solution was then extracted with EtOAc (3×75 ml). The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the crude title compound (4.4 g). MS m/z (rel. intensity, 70 eV) 245 (M+, 97) 244 (M+, bp), 189 (48), 188 (50) 70 (39).

Fuente