反応 #8184

反応方程式

2-nitropropane

7-benzyloxy gramine

NaOH

2-nitropropane

→

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

収率 92.1%

溶媒

Ether

反応条件

後処理

1. 1
   温度is heated to reflux
2. 2
   温度After 10 minutes at reflux
3. 3
   ろ過the mixture is filtered
4. 4
   workup.ADDITIONThe filtrate is treated with 10% acetic acid (6 mL)
5. 5
   その他the layers are separated
6. 6
   洗浄the organic layer is rinsed with water (2×25 mL)
7. 7
   乾燥The organic layer is dried (Na2SO4)
8. 8
   濃縮concentrated

実験手順

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.

出典