2-Cyclohexen-1-one → 3-(4-(1,1-Dimethylethyl)phenyl)cyclohexanone

Participants

Reaction Conditions

Reaction Steps

To a 40 mL microwave flask containing 10/1 dioxane/H2O (22 mL) was added cyclohexen-1-one (1.35 g, 14.0 mmol), acetylacetonatobis(ethylene)rhodium(I) (0.36 g, 1.40 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.88 g, 1.40 mmol) and 4-tert-butylphenylboronic acid (5.0 g, 28.0 mmol). The reaction mixture was heated in the microwave at 100° C. for 20 minutes. The material was poured into a separatory funnel and extracted with ethyl acetate (150 mL), washed with saturated aqueous NaHCO3 (75 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (20% EtOAc/hexanes) to afford the title compound (1.97 g, 61%) as a yellow oil. 1H NMR (CD3OD, 300 MHz) δ 1.30 (s, 9H), 1.68-2.17 (m, 4H), 2.32-2.38 (m, 3H), 2.64 (dt, J=1.01, 12.0 Hz, 1H), 2.91-3.01 (m, 1H), 7.11-7.20 (m, 2H), 7.31-7.36 (m, 2H); MS (DCI) m/z 248 (M+H)+.

Provenance & Evidence