Реакция #532853

Уравнение реакции

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

iPrMgCl

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

title compound

1-[2-(Tetrahydro-pyran-2-yloxy)-ethyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe solution was stirred again
2. 2
   Температураto warm to rt for 1 h
3. 3
   ДругоеAfter that, the RM was quenched with saturated aqueous NH4Cl (140 ml)
4. 4
   Экстракцияextracted with EtOAc (3×)
5. 5
   ПромывкаThe combined organic layers were washed with saturated aqueous NH4Cl
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   ДругоеThe residue was purified by flash chromatography (hexane/EtOAc 5% to 45%)
10. 10
    workup.ADDITIONThe fractions containing product
11. 11
    Другоеevaporated to dryness

Методика

To a solution of 4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole (Stage 106.1.3, 8.50 g, 26.4 mmol) in THF at 0° C. under argon was added dropwise iPrMgCl 2 M in THF (26.4 ml, 52.8 mmol). The RM was stirred at 0° C. for 1 h. Then 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Aldrich, Buchs, Switzerland, 6.25 g, 52.8 mmol) was added at 0° C. and the solution was stirred again and allowed to warm to rt for 1 h. After that, the RM was quenched with saturated aqueous NH4Cl (140 ml) and extracted with EtOAc (3×). The combined organic layers were washed with saturated aqueous NH4Cl, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (hexane/EtOAc 5% to 45%). The fractions containing product were combined and evaporated to dryness to give the title compound as a colorless oil. (HPLC: tR 3.23 min (Method A); M+H=323 MS-ES)

Источник