Cyclopropanecarboxaldehyde → (4-Chloro-3-methyl-2-pyridyl)-cyclopropyl-methanol
反応式
Br[C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[CH:15]1([CH:18]=[O:19])[CH2:17][CH2:16]1>C1COCC1>[CH3:8][C:7]1[C:2]([CH:18]([CH:15]2[CH2:17][CH2:16]2)[OH:19])=[N:3][CH:4]=[CH:5][C:6]=1[Cl:9]参加物
5
実験手順
A solution of 2-bromo-3-methyl-4-chloro-pyridine (10.6 g, 57.1 mmol) in freshly distilled THF (120 mL) was cooled down to 0° C. and treated with isopropyl magnesium chloride (45.7 mL, 2.0 M in THF, 91.5 mmol). The resulting mixture was stirred at room temperature for 3 h then cooled to −5° C. Cyclopropane carboxaldehyde (6.83 mL, 91.5 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and quenched by adding water (100 mL), and extracted with ethyl acetate (2×150 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1) to afford the title compound as a yellow oil (7.01 g, 62%).