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

Participants

Reaction Steps

A solution of 4-[1-allyl-1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxymethyl)-but-3-enyl]-benzoic acid methyl ester (6.0 mL of 0.11M stock solution in CH2Cl2, 0.578 g, 1.14 mmol) in CH2Cl2 (570 mL) is treated with [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)-(tricyclohexylphosphine)ruthenium] (0.101 g, 0.1192 mmol) at 35° C. for 1 h, cooled to room temperature, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford the title compound (0.458 g, 84%) as a colorless syrup. 1H NMR (CDCl3): δ 7.98-7.96 (m, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.44-7.41 (m, 2H), 7.20 (d, J=8.1 Hz, 2H), 6.58 (s, 2H), 5.77 (s, 2H), 3.99 (s, 2H), 3.89 (s, 3H), 2.87 (d, J=14.3 Hz, 2H), 2.77 (d, J=14.9 Hz, 2H), 1.92 (s, 6H).

Provenance & Evidence