Toluene → (+/-)-1-(Biphenyl-3-yloxy)-4-(3-pyridyl)-2-butanol

Participants

Reaction Steps

Prepared according to the method described in Example 33a) from toluene (5 ml), aqueous sodium carbonate (2 M, 1 ml), (±)-1-(3-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.25 g), ethanol (1 ml), benzeneboronic acid (0.14 g) and tetrakis(triphenylphosphine)palladium(0) (30 mg) with heating at reflux for 4 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate to give (±)-1-(biphenyl-3-yloxy)-4-(3-pyridyl)-2-butanol as a colourless oil (0.178 g). Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic gave the title compound as a hygroscopic gum. (0.10 g)

Provenance & Evidence