Реакция #627142

Уравнение реакции

sodium bicarbonate

trimethylsilyl-formonitrile

dibenzylamine

dihydrofuran-3(2H)-one

→

desired product

Выход 9.3%

3-(Dibenzylamino)tetrahydrofuran-3-carbonitrile

Выход 9.3%

Растворители

ethyl acetate

water

acetic acid

Условия реакции

Обработка

1. 1
   ПромывкаThe combined organic layers were washed with brine (150 mL)
2. 2
   Сушкаdried over sodium sulfate
3. 3
   Концентрированиеconcentrated in vacuo
4. 4
   ДругоеThe residue was purified by column chromatography

Методика

To a cooled solution of dibenzylamine (31.9 g, 162 mmol) in acetic acid (100 mL) at 0° C., dihydrofuran-3(2H)-one (7.0 g, 81 mmol) was added followed by trimethylsilyl-formonitrile (14.4 g, 145.8 mmol). After being stirred at room temperature for 16 hours, the reaction mixture was poured into water (100 mL), adjusted to pH 7 with sodium bicarbonate, exacted with ethyl acetate (100 mL×2). The combined organic layers were washed with brine (150 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to afford 2.2 g of the desired product (yield was 9.28%).

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