3-Nitrophenylboronic Acid → (2R)-1-(3'-nitrobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Participants

Reaction Conditions

Reaction Steps

Prepared according to the method described in Example 33a) from toluene (5 ml), aqueous sodium carbonate (2 M, 1 ml), (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.31 g) ethanol (1 ml), 3-nitrobenzeneboronic acid (0.24 g) and tetrakis(triphenylphosphine)palladium(0) (30 mg) with heating at 110° C. for 4 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate to give (2R)-1-(3'-nitrobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol as a yellow oil (0.210 g). Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic acid gave the title compound as a hygroscopic gum (0.150 g).

Provenance & Evidence