Triphenylphosphine → 4-[1-Allyl-1-(2,6-dimethyl-4'-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(1-allyl-1-hydroxymethyl-but-3-enyl)-benzoic acid methyl ester (0.768 g, 2.95 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.861 g, 3.23 mmol), and triphenylphosphine (1.180 g, 4.50 mmol) in toluene (30 mL) is treated with 1,1′-(azodicarbonyl)-dipiperidine (1.182 g, 4.68 mmol) and stirred overnight at 80° C. The reaction mixture is then cooled to room temperature, diluted with MeOH, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% EtOAc to 40% EtOAc to provide 0.964 g (64%) of the title compound as a clear syrup. 1H NMR (CDCl3): δ 8.02-8.00 (m, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.46-7.44 (m, 2H), 7.26 (d, J=7.8 Hz, 2H), 6.68 (s, 2H), 5.60-5.54 (m, 2H), 5.08-5.00 (m, 4H), 4.15 (s, 2H), 3.91 (s, 3H), 2.66 (d, J=7.6 Hz, 4H), 1.99 (s, 6H).

Provenance & Evidence