反応 #1384238

反応方程式

water

Potassium carbonate

4-nitrophenol

13

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

→

product

収率 77.1%

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

収率 77.1%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   抽出extracted three times with methylene chloride
3. 3
   洗浄The combined organic layers were washed with water
4. 4
   乾燥brine, dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他the solvent was removed by distillation at reduced pressure

実験手順

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.

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