Реакция #805353

Уравнение реакции

4-iodopyrazole

Cs2CO3

2-(2-bromoethoxy)tetrahydro-2H pyran

→

4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole

Выход 66.2%

Растворители

EtOAc

water

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe resultant reaction mixture
2. 2
   ДругоеThe layers were separated
3. 3
   Экстракцияthe aqueous layer was extracted with EtOAc (3×500 mL)
4. 4
   ПромывкаThe combined organic layers were washed with water
5. 5
   Сушкаdried over Na2SO4
6. 6
   Концентрированиеconcentrated
7. 7
   Другоеto afford yellow oil
8. 8
   ДругоеPurification on a silica gel

Методика

A solution of 4-iodopyrazole (20 g, 0.10 mol) in anhydrous DMF (300 mL) was treated with Cs2CO3 (32.5 g, 0.10 mol) and 2-(2-bromoethoxy)tetrahydro-2H pyran. The resultant reaction mixture was stirred at 70° C. overnight. The cooled mixture was diluted with EtOAc (500 mL) and water (500 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×500 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated to afford yellow oil. Purification on a silica gel provided 4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole (22 g, 66.2% yield). 1H-NMR (300 MHz, CDCl3): δ 7.55 (s, 1H), 7.50 (s, 1H), 4.53 (s, 1H), 4.33 (m, 2H), 4.03 (m, 1H), 3.74 (m, 1H), 3.61 (m, 1H), 3.46 (m, 1H), 1.60-1.48 (m, 6H).

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