Reacción #357700

Ecuación de reacción

NH4Cl

lithium hydride

2-hydroxyacetophenone

MOM-Cl

→

product

Rendimiento 45.6%

2-(methoxymethoxy)-1-phenylethanone

Rendimiento 45.6%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas stirred for 16 hours
2. 2
   Extracciónextracted with ethyl acetate (3×50 mL)
3. 3
   LavadoThe combined organics were washed with water (6×50 mL) and brine (50 mL)
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe brown residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate)

Procedimiento

To a cooled (0° C.) solution of 2-hydroxyacetophenone (1.0 g, 7.3 mmol) in DMF (50 mL) was added lithium hydride (74 mg, 95%, 8.8 mmol). After stirring for 30 minutes, MOM-Cl (0.73 mL, 9.5 mmol) was added slowly via syringe and the mixture was allowed to warm slowly to room temperature and was stirred for 16 hours. The reaction mixture was treated with saturated NH4Cl (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (6×50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The brown residue was chromatographed (9:1 to 4:1 hexanes/ethyl acetate) to provide the product as a colorless oil (0.60 g, 45%).

Fuente