Реакция #555254

Уравнение реакции

NH4Cl

lithium hydride

2-hydroxyacetophenone

MOM-Cl

→

product

Выход 45.6%

2-(methoxymethoxy)-1-phenylethanone

Выход 45.6%

Растворители

DMF

Условия реакции

Обработка

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

Методика

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%).

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