Ethylene Glycol → HCID 59545167, compound

Participants

Reaction Conditions

Reaction Steps

20 g (76 mmole) 7-Chloro-2-cyclohexylmethyl-indan-1-one, 13.7 g (1.2 eq.) 2,3-dimethylphenyl boronic acid, 17.75 g sodium carbonate, 250 ml ethylene glycol and 50 ml water were placed in a 1 l-roundbottom flask equipped with a mechanical stirrer and a reflux condenser. The mixture was degassed three times by slight evacuation and recharging with argon. A premixed catalyst solution consisting of 34 mg (0.2 mole %) palladium acetate, 1 ml NaTPPTS (2.6 M in water, 0.8 mole %) and 2 ml of water was added and the mixture was refluxed at 125° C. until complete conversion (approx. 4 h). 100 ml of water were added and the mixture was extracted three times with 100 ml of toluene each. The combined organic layers were washed twice with 100 ml water and once with 100 ml of a saturated sodium chloride solution. Drying over magnesium sulphate and evaporation of the solvent in vacuo yielded 27.7 g (quant.) of the desired product as a yellow sticky oil. 1H-NMR (400 MHz, CDCl3): δ=7.55 (t, 1H, aromatic), 7.39 (d, 1H, aromatic), 7.28-7.02 (m, 3H, aromatic), 3.34 (m, 1H, (C═O)CH), 2.81-2.69 (m, 2H, benzylic), 2.37 (s, 6H, Ph-CH3), 1.89-0.89 (m, 10H, aliphatic) ppm.

Provenance & Evidence