تفاعل #725869

معادلة التفاعل

water

Potassium carbonate

4-nitrophenol

13

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

→

product

المردود 77.1%

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

المردود 77.1%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   استخلاصextracted three times with methylene chloride
3. 3
   غسيلThe combined organic layers were washed with water
4. 4
   تجفيفbrine, dried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent was removed by distillation at reduced pressure

الإجراء التجريبي

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.

المصدر