反应 #725869

反应方程式

water

Potassium carbonate

4-nitrophenol

13

2-[2-(2-methoxyethoxy)ethoxy]ethyl p-toluenesulfonate

→

product

收率 77.1%

4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}nitrobenzene

收率 77.1%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   萃取extracted three times with methylene chloride
3. 3
   洗涤The combined organic layers were washed with water
4. 4
   干燥brine, dried over magnesium sulfate
5. 5
   过滤filtered
6. 6
   其他the solvent was removed by distillation at reduced pressure

实验过程

A portion of 13 (9.0 g, 28.3 mmol) was dissolved in 50 mL of dimethylformamide. Potassium carbonate (11.75 g, 85.0 mmol) and 4-nitrophenol (3.82 g, 27.5 mmol) were added. The solution was stirred at 80° C. for 16 hours. After cooling to room temperature, the solution was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with water, then brine, dried over magnesium sulfate, filtered, and the solvent was removed by distillation at reduced pressure. Chromatography (silica, hexane:ethyl acetate, 1:2) was employed to isolate the product (5.71 g, 73% yield). IR (neat) 3109.2, 3078.2, 2878.5, 1726.3, 1588.1, 1511.2, 1337.1, 1106.7, 1050.3, 932.6, 845.5, 753.3, 656.1 cm−1. 1H NMR (CDCl3) δ 8.07 (d, J=9.3 Hz, 2H), 6.88 (d, J=9.3 Hz, 2H), 4.12 (app t, 2H), 3.79 (app t, 2H), 3.62 (m, 2H), 3.58 to 3.53 (m, 4H), 3.44 to 3.42 (m, 2H), 3.26 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 164.29, 141.93, 126.24, 114.99, 72.29, 71.29, 71.03, 70.98, 69.77, 68.60, 59.44.

来源