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

Participants

Reaction Steps

To a dimethyl sulfoxide solution (150 mL) of acetic acid (7.4 mL) and 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (30.8 g, 120 mmol)) described in Manufacturing Example 1-2-3 was added sodium borohydride (2.45 g, 64.8 mmol) at 30° C. or lower. The reaction solution was stirred for 40 minutes at room temperature. Water, ethyl acetate, and diethyl ether were added at 30° C. or lower to the reaction solution, to separate the reaction solution into water and an organic layer. The aqueous layer was extracted with ethyl acetate. The previously obtained organic layer and the ethyl acetate layer obtained this time were combined, washed with water three times and saline once, dried over anhydrous magnesium sulfate, and filtered. This filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (15.2 g).

Provenance & Evidence