Dimethylformamide → 4-((Pyridin-2-yloxy)methyl)benzaldehyde

Participants

Reaction Steps

To a tetrahydrofuran solution (120 mL) of 2-(4-bromo-benzyloxy)-pyridine described in Preparation Example 1-4-1 (34 g, 128 mmol) was added n-butyl lithium (50 mL, 2.6M hexane solution, 134 mmol) dropwise at −78° C. After stirring for 30 minutes, to this reaction solution was added N,N-dimethylformamide (10 mL, 134 mmol) dropwise at −78° C, which was stirred at room temperature. To the reaction solution were added water and ethyl acetate to carry out liquid separation. The ethyl acetate layer was washed with water (twice) and sodium chloride water (once). The aqueous layers were combined and extracted with ethyl acetate. The resulting ethyl acetate layer was washed with water (twice) and sodium chloride water (once). The ethyl acetate layer obtained earlier and the ethyl acetate layer obtained this time were combined, dried over anhydrous magnesium sulfate and then filtered. The filtrate thereof was concentrated under a reduced pressure to obtain the title compound (26.8 g) as a crude product.

Provenance & Evidence