Sodium Carbonate → 2-Methyl-7-phenyl-1-indanone

Participants

Reaction Conditions

Reaction Steps

2.5 g (13.8 mmol) of 7-chloro-2-methyl-1-indanone (1), 2.11 g (17.3 mmol) of phenylboronic acid and 3.66 g (34.6 mmol) of sodium carbonate were placed in 40 ml of o-xylene/5 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 1.55 mg (0.0069 mmol) of palladium acetate and 7.3 mg (0.027 mmol) of triphenylphosphine, the reaction mixture was stirred for 8 hours at 100° C. After 2, 4 and 6 hours, the same amount of palladium acetate and triphenylphosphine were added again each time. After addition of 40 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 40 ml each time of ether, the combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 2.9 g of (15) as solid. The 1H-NMR indicated a conversion of about 85%.

Provenance & Evidence