Reaktion #1013671

Reaktionsgleichung

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched with saturated aqueous ammonium chloride solution
2. 2
   SonstigeThe mixture was partitioned between water and ethyl acetate
3. 3
   ExtraktionThe separated aqueous phase was further extracted with ethyl acetate
4. 4
   Waschenwashed with saturated aqueous NaCl solution
5. 5
   TrocknenThe organic phase was dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product was purified by flash column chromatography (silica gel, 0-10% MeOH-DCM)

Vorschrift

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.

Quelle