Chloride → HCID 71114876, compound

Participants

Reaction Steps

Bis(1,5-cyclooctadienerhodium chloride) (1.09 g, 2.18 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3.05 g, 4.90 mmol) are added to tetrahydrofuran (72 mL) and the mixture is stirred under a nitrogen atmosphere for 30 minutes. This solution is added to a mixture of 4-cyanophenylboronic acid (80.04 g, 544.68 mmol), 5,5-dimethylcyclopent-2-en-1-one (24 g, 217.87 mmol), potassium carbonate (40.65 g, 294.13 mmol), tetrahydrofuran (144 mL), and isopropyl alcohol (16.7 mL) at 60° C. The mixture is stirred at 60° C. for 16 hours and then concentrated to dryness. The crude mixture is poured into water (500 mL) and is extracted with ethyl acetate (2×500 mL). The organic extracts are dried over MgSO4, filtered through silica gel, and concentrated to dryness. The residue is purified by silica gel flash chromatography, eluting with 6:1 hexane:ethyl acetate to give the title compound (41 g, 88%, 192.24 mmol). 1H NMR (300.13 MHz, CDCl3) δ 7.65-7.62 (m, 2H), 7.37 (d, J=8.1 Hz, 2H), 3.56-3.43 (m, 1H), 2.86-2.76 (m, 1H), 2.42-2.32 (m, 1H), 2.32-2.24 (m, 1H), 1.86 (t, J=12.4 Hz, 1H), 1.17 (s, 3H), 1.15 (s, 3H).

Provenance & Evidence