Chloride → HCID 71114821, compound

Participants

Reaction Steps

Bis(1,5-cyclooctadienerhodium chloride) (0.06 g, 0.12 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.18 g, 0.29 mmol) are added to tetrahydrofuran (40 mL) and the mixture is stirred under a nitrogen atmosphere for 30 minutes. This solution is added to a mixture of 4-cyanophenylboronic acid (2.31 g, 15.69 mmol), 6-methylcyclohex-2-en-1-one (Journal of Organic Chemistry, 1980 45(10), 1852-1863) (1.28 g, 11.62 mmol), potassium carbonate (2.19 g, 15.69 mmol), and isopropyl alcohol (1.1 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 (10 mL) and is extracted with ethyl acetate (2×20 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 20% EtOAc/hexane to give (trans)-4-(4-methyl-3-oxo-cyclohexyl)benzonitrile (0.55 g, 22%) as the first eluting isomer and (cis)-4-(4-methyl-3-oxo-cyclohexyl)benzonitrile (0.55 g, 22%) as the second eluting isomer. ES/MS m/z 214 (M+H).

Provenance & Evidence