Реакция #2146778

Уравнение реакции

4-methoxy-benzyl chloride

hydrogen

4-iodo-1H-pyrazole

sodium hydride

→

product

Выход 93.1%

4-Iodo-1-(4-methoxy-benzyl)-1H-pyrazole

Выход 93.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеquenched with water (50 mL)
2. 2
   Экстракцияextracted with diethyl ether (100 mL)
3. 3
   ПромывкаThe organic layer was washed with water (3×30 mL) and brine
4. 4
   Сушкаdried over magnesium sulphate
5. 5
   Другоеthe solvent removed under vacuum
6. 6
   ПромывкаThe crude residue was washed with small portions of hexane
7. 7
   Другоеdried in vacuo

Методика

To a stirred solution of 4-iodo-1H-pyrazole (1.50 g, 7.73 mmol) in dry DMF (15 mL) at 0° C. was added sodium hydride (9.28 mmol, 60% dispersion in mineral oil) and the reaction mixture was allowed to warm to room temperature. After the evolution of hydrogen had ceased, 4-methoxy-benzyl chloride (1.06 mL, 7.80 mmol) was added and the reaction was stirred for 2 h and then quenched with water (50 mL) and extracted with diethyl ether (100 mL). The organic layer was washed with water (3×30 mL) and brine, dried over magnesium sulphate and the solvent removed under vacuum. The crude residue was washed with small portions of hexane and dried in vacuo, providing the product as a white solid (2.26 g, 93% yield). 1H-NMR (CDCl3) δ 7.51 (s, 1H), 7.34 (s, 1H), 7.17 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 5.21 (s, 2H), 3.78 (s, 3H).

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