Tri-o-tolylphosphine → HCID 21830726, compound

Participants

Reaction Steps

Prepared according to the method described in Example 7b) from (±)-5-(3-pyridyl)-1-penten-3-ol (Example 7a, 0.66 g), 3'-chloro-4-trifluoromethanesulfonyloxybiphenyl (1.34 g), palladium(II) acetate (0.09 g), tri-o-tolylphosphine (5 ml) and triethylamine (1 ml) at 80° C. for 5 hours. Work up and purification by column chromatography over silica eluting with dichloromethane:methanol (19:1) gave (±)-1-(3'-chlorobiphenyl-4-yl)-5-(3-pyridyl)-3-pentanone (0.4 g). The latter was immediately dissolved in methanol (10 ml), cooled to 0° C. and sodium borohydride (0.043 g) added. The reaction mixture was stirred at 25° C. for 2 hours and was then concentrated under reduced pressure. Water was added to the residue and the mixture extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate. Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic acid gave the title compound as a solid (0.094 g).

Provenance & Evidence