Реакция #1013671

Уравнение реакции

1-methyl-1H-imidazole-5-carbaldehyde

isopropylmagnesium chloride lithium chloride

4-bromo-2-(trifluoromethyl)pyridine

→

title compound

(1-Methyl-1H-imidazol-5-yl)(2-(trifluoromethyl)pyridin-4-yl)methanol

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеwas quenched with saturated aqueous ammonium chloride solution
2. 2
   ДругоеThe mixture was partitioned between water and ethyl acetate
3. 3
   ЭкстракцияThe separated aqueous phase was further extracted with ethyl acetate
4. 4
   Промывкаwashed with saturated aqueous NaCl solution
5. 5
   СушкаThe organic phase was dried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM)

Методика

A solution of isopropylmagnesium chloride/lithium chloride complex (1.3 M in THF, 10.6 mL, 13.8 mmol) was added dropwise by syringe to a solution of 4-bromo-2-(trifluoromethyl)pyridine (3.12 g, 13.8 mmol) in dry THF (50 mL) at 0° C. After 30 minutes, a solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.38 g, 12.5 mmol) in THF (28.5 mL) was added to the Grignard solution by syringe at 0° C. The reaction mixture was warmed to room temperature over 2 hours after which it was quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate and washed with saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM) to provide the title compound.

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