반응 #357700

반응 방정식

NH4Cl

lithium hydride

2-hydroxyacetophenone

MOM-Cl

→

product

수율 45.6%

2-(methoxymethoxy)-1-phenylethanone

수율 45.6%

용매

DMF

반응 조건

후처리

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

실험 절차

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%).

출처