Реакция #44296
ord-9b0994932db2441089ec9ce62e502733
Уравнение реакции
Реактанты
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Условия реакции
Обработка
- 1workup.STIRRINGto stir for 1 hour at ambient temperature under nitrogen
- 2ДругоеThe reaction was quenched with sat. aqueous solution of NH4Cl (10 mL)
- 3workup.ADDITIONwere added
- 4ДругоеThe organic layer was separated
- 5Экстракцияthe aqueous layer was extracted with EtOAc (3×50 mL)
- 6Сушкаdried over Na2SO4
- 7Концентрированиеconcentrated
- 8Другоеto give the crude product as yellow oil
- 9ДругоеThe oil was purified a silica gel column
- 10Промывкаeluting with EtOAc and hexanes
Методика
To a solution of 4-iodo-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazole (1.0 g, 3.1 mmol) in anhydrous THF (8 mL) was added iPrMgCl (2M in THF, 3.10 mL, 6.21 mmol) at 0° C. drop by drop under nitrogen. The reaction was stirred for 1 hour at 0° C. under nitrogen. To the solution was added 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.736 g, 4.66 mmoL) at 0° C. and the resulting yellow solution was allowed to stir for 1 hour at ambient temperature under nitrogen. The reaction was quenched with sat. aqueous solution of NH4Cl (10 mL). EtOAc (50 mL) and sat aqueous NH4Cl solution (10 mL) were added. The organic layer was separated, and the aqueous layer was extracted with EtOAc (3×50 mL), dried over Na2SO4, and concentrated to give the crude product as yellow oil. The oil was purified a silica gel column eluting with EtOAc and hexanes to provide 1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole as clear oil (800 mgs, 80% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.91 (s, 1H) 4.48-4.54 (m, 1H) 4.26-4.33 (m, 2H) 3.86-3.90 (m, 1H) 3.66-3.76 (m, 1H) 3.45-3.57 (m, 1H) 3.33-3.39 (m, 1H) 1.33-1.70 (m, 6H) 1.24 (s, 12H).