Реакция #163637

Уравнение реакции

Diethyl 2-bromo-2-methylmalonate

potassium fluoride

3-nitrophenol

→

diethyl 2-methyl-2-(3-nitrophenoxy)malonate

Выход 80.0%

Растворители

DMF

water

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe resulting mixture was stirred at 60° C. for 6 h
2. 2
   Температураcooled to room temperature
3. 3
   Экстракцияextracted with ethyl acetate (3×200 mL)
4. 4
   ПромывкаThe organic layer was washed with aq. 1N NaOH (2×75 mL)
5. 5
   Сушкаdried over anhydrous Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated in vacuo

Методика

Diethyl 2-bromo-2-methylmalonate (1.0 g, 3.95 mmole) was added to a stirred suspension of potassium fluoride (0.57 g, 9.8 mmole) in dry DMF (5 mL). After stirring for 20 min at room temperature, 3-nitrophenol (0.55 g, 3.95 mmole) was added. The resulting mixture was stirred at 60° C. for 6 h, cooled to room temperature, diluted with water (30 mL) and extracted with ethyl acetate (3×200 mL). The organic layer was washed with aq. 1N NaOH (2×75 mL), dried over anhydrous Na2SO4, filtered and evaporated in vacuo to provide diethyl 2-methyl-2-(3-nitrophenoxy)malonate (0.89 g, 80%). 1H NMR (CDCl3): δ 7.92 (dd, 1H, J=2.3 and 8.2 Hz), 7.82 (t, 1H, J=2.3 Hz), 7.41 (t, 1H, J=8.2 Hz), 7.30 (dd, 1H, J=2.3 and 8.2 Hz), 4.28 (qt, 4H, J=7.0 Hz), 1.81 (s, 3H), 1.26 (t, 6H, J=7.0 Hz).

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