Reacción #172355

Ecuación de reacción

(R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane

3-Nitrophenol

potassium carbonate

→

desired product 132

Rendimiento 52.0%

(R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane

Rendimiento 52.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Temperaturawas heated in the microwave reactor
3. 3
   OtroThe crude reaction mixture
4. 4
   Lavadowas rinsed with water
5. 5
   Filtraciónfiltered
6. 6
   Extracciónextracted with dichloromethane (3×15 mL)
7. 7
   SecadoThe combined organic layers were dried (Na2SO4)
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe resulting residue was purified by chromatography

Procedimiento

3-Nitrophenol (130; 2.0 g, 14.37 mmol) was taken up in 20 mL of anhydrous DMF along with anhydrous potassium carbonate (4.96 g, 35.93 mmol) and (R)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (131; 2.55 mL, 18.68 mmol). The resulting reaction mixture was heated in the microwave reactor, with stirring, at 160° C. for 4 h. The crude reaction mixture was rinsed with water, filtered and extracted with dichloromethane (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography using ethyl acetate:pentanes to obtain the desired product 132 as an amber-colored oil (52%).

Fuente