Reacción #156396

Ecuación de reacción

4-iodopyrazole

cesium carbonate

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

→

title compound

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheating at 70° C. for 17 h
2. 2
   OtroThen the RM was quenched with 100 mL water
3. 3
   Extracciónextracted with 3×120 mL EtOAc
4. 4
   LavadoThe combined organic layers were washed with 3×100 mL water and 1×100 mL brine
5. 5
   Secadobefore being dried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated to dryness
8. 8
   OtroThe residue was purified by flash chromatography (6×25 cm, Hexane/EtOAc 0%-30%)

Procedimiento

In flask were introduced 4-iodopyrazole (10 g, 51.6 mmol), cesium carbonate (20.16 g, 61.9 mmol) and anhydrous DMF (98 mL). The suspension was stirred at rt for 5 min, before adding 2-(2-bromoethoxy)tetrahydro-2H-pyran (9.74 mL, 61.9 mmol) and heating at 70° C. for 17 h. Then the RM was quenched with 100 mL water and extracted with 3×120 mL EtOAc. The combined organic layers were washed with 3×100 mL water and 1×100 mL brine, before being dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (6×25 cm, Hexane/EtOAc 0%-30%) to afford the title compound as a colorless oil (tR 3.12 min (conditions 8), MH+=323).

Fuente