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EXAMPLE 1 Synthesis of 2-Methyl-4-(2,6-Dimethylphenyl)Indene Reaction Procedure A flask is charged with palladium (II) acetate (18.5 mg, 0.08 mmol), 2-(dicyclohexylphosphino)-2'-methyl biphenyl (94 mg, 0.26 mmol), (2,6-dimethylphenyl) boronic acid (1.7 g, 11.3 mmol, freshly recrystallized from Et2O/hexane) (synthesised according to literature, J.Am.Chem.Soc. (1960) 82:3053-3059), and potassium phosphate (3.1 g, 14.6 mmol). The flask is filled with nitrogen before addition of dry deoxygenated toluene (14 mL) and 2-methyl-4-chloroindene (1.3 g, 7.9 mmol) (synthesised according to U.S. Pat. No. 5,789,634) via syringe under nitrogen. The mixture was stirred at 100 C. for 20 hours under nitrogen. Analysis of an aliquot by GC/MS revealed a 66% yield of desired product and 33% of starting 2-methyl-4-chloroindene. The reaction was cooled to ambient temperature, diluted with diethyl ether and washed with aqueous saturated sodium bicarbonate. The organic phase was dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by chromatography on silica gel eluted with hexane to afford 0.9 grams (49% isolated yield) of 2-methyl-4-(2,6-dimethylphenyl)indene as a pale yellow waxy solid, a 1:1 mixture of the two olefin isomers by proton NMR. Data: TLC Rf0.3 (hexane); observed M+234, calculated 234; 1H NMR (250 MHz, CD2Cl2) 7.35-7.13 (m, 5H), 6.96 (d, 0.5H), 6.84 (d, 0.5H), 6.81 (dd, 0.5H), 5.99 (br t, 0.5 H), 3.39 (s, 1H), 2.89 (s, 1H), 2.09 (s, 3H), 1.97 (s, 6H). |