Toluene → Bis[2-(cyclohexylmethyl)-4-(4-tert-butylphenyl)-1,5,6,7-tetrahydro-s-indacen-1-yl](dimethyl)silane

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Reaction Conditions

Reaction Steps

To a solution of 20.8 g (54.1 mmol) of 4-(4-tert-butylphenyl)-6-(cyclohexylmethyl)-1,2,3,5-tetrahydro-s-indacene in 600 ml of toluene 21.7 ml (54.2 mmol) of 2.5 M nBuLi in hexanes was added dropwise at 20° C. Then, 30 ml of THF was added, and the resulting mixture was stirred for 1 h at 70° C. The resulting mixture was cooled to 0° C., and 3.30 ml (3.49 g, 27.1 mmol) of dichlorodimethylsilane was added. This mixture was stirred for 12 h at room temperature, then 5 ml of water was added, and organic solvents were evaporated using Rotavapor. The product was extracted from the residue by 3×100 ml of dichloromethane. The organic extract was dried over Na2SO4 and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: hexanes and then hexanes-dichloromethane, 10:1, vol.). Yield 15.2 g (68%).

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