Ethylene Glycol → HCID 21951285, compound

Participants

Reaction Conditions

Reaction Steps

13.4 g (68.8 mmol) of 7-chloro-2,4-dimethyl-1-indanone (1c), 14.71 g (82.6 mmol) of 4-tert-butylphenylboronic acid, 16.05 g (151 mmol) of sodium carbonate, 188 ml of ethylene glycol and 30.7 ml of water were placed in a reaction vessel under a protective gas atmosphere and the mixture was heated to 80° C. While stirring vigorously, a freshly prepared catalyst solution comprising 77 mg (0.343 mmol) of palladium acetate and 1.7 ml (1.01 mmol) of an aqueous TPPTS solution (0.6 molar) in 25 ml of water was added to the reaction components and the reaction mixture was refluxed for 3 hours until the reaction was complete. After cooling to room temperature, the ethylene glycol phase was extracted three times with a total of 900 ml of toluene. The combined toluene phases were washed twice with a total of 250 ml of sodium chloride solution and dried over 150 g of sodium sulfate. Removal of the solvent and drying of the residue and subsequent distillation in an oil pump vacuum gave 18.59 g of (1d).

Provenance & Evidence