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

Temperature

100 °C

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)+.

1. additionThe material was poured into a separatory funnel
2. extractionextracted with ethyl acetate (150 mL)
3. washwashed with saturated aqueous NaHCO3 (75 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by silica gel chromatography (20% EtOAc/hexanes)

ORD record

ord-21d60a7a81254c59987b23ea2640c7cf

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802711B2