Reaktion #357700

Reaktionsgleichung

NH4Cl

lithium hydride

2-hydroxyacetophenone

MOM-Cl

→

product

Ausbeute 45.6%

2-(methoxymethoxy)-1-phenylethanone

Ausbeute 45.6%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle