Acetic Acid → 2-((4-(2-Nitroethyl)benzyl)oxy)pyridine

Participants

Reaction Steps

To a solution of 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine described in Preparation Example 1-3-3 (21.0 g, 81.9 mmol), acetic acid (21 mL) and dimethylsulfoxide (200 mL) was added sodium borohydride (4.96 g, 131 mmol), while being suitably cooled at room temperature. After sodium borohydride was added, the cold bath was removed, the solution was stirred at room temperature for 15 minutes. The reaction solution was partitioned into water and ethyl acetate. The ethyl acetate layer was washed twice with water and once with sodium chloride water, this was dried over anhydrous magnesium sulfate, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (16.3 g).

Provenance & Evidence