Water → 4-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

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Reaction Steps

0.3 g of palladium acetate (3 mol %) and 0.7 g of triphenylphosphine (6 mol %) were added to a well-stirred mixture of 12 g (0.045 mol) of 4-bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1b), 11.2 g (0.063 mol) of tert-butylphenylboronic acid and 13.4 g (0.126 mol) of sodium carbonate in 170 ml of dimethoxyethane (DME)/56 ml of water. The reaction mixture was refluxed for 6 hours, poured into water and extracted with methylene chloride (5×100 ml). The combined organic phases were washed with sodium carbonate solution and water and dried over magnesium sulfate. After removal of the solvent, the crude product was chromatographed on silica gel (hexane/chloroform from 4/1 to 1/1). This gave 10 g (70% yield) of the compound (1c) as a viscous oil.

Provenance & Evidence