Реакция #8184

Уравнение реакции

2-nitropropane

7-benzyloxy gramine

NaOH

2-nitropropane

→

3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole

Выход 92.1%

Растворители

Ether

Условия реакции

Обработка

1. 1
   Температураis heated to reflux
2. 2
   ТемператураAfter 10 minutes at reflux
3. 3
   Фильтрацияthe mixture is filtered
4. 4
   workup.ADDITIONThe filtrate is treated with 10% acetic acid (6 mL)
5. 5
   Другоеthe layers are separated
6. 6
   Промывкаthe organic layer is rinsed with water (2×25 mL)
7. 7
   СушкаThe organic layer is dried (Na2SO4)
8. 8
   Концентрированиеconcentrated

Методика

A mixture of 7-benzyloxy gramine (1.99 g, 7.10 mmol), solid NaOH (298 mg, 7.22 mmol) and 2-nitropropane (4.5 mL, 50 mmol) is heated to reflux. After 10 minutes at reflux, a thick slurry developed which is difficult to stir. Gas evolution is observed, and an additional 1 mL of 2-nitropropane is added to loosen the mixture. After 29 hours, the mixture is allowed to cool to ambient temperature. Ether (30 mL) is added and the mixture is filtered. The filtrate is treated with 10% acetic acid (6 mL), the layers are separated and the organic layer is rinsed with water (2×25 mL). The organic layer is dried (Na2SO4) and concentrated to give 2.12 g of 3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole (92%). MS (ES+) m/z 325.

Источник