Ammonium Chloride → Dimethyl-(6-methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-(4-t-butylphenyl)-1-indenyl)silane

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Reaction Steps

To 11.4 g (35.3 mmol) of 6-methyl-4,8-diphenyl-1,2,3,5-tetrahydro-s-indacene (5c) and 100 mg of copper cyanide (I) in 300 ml of diethylether plus 20 ml of THF was added dropwise at −70° C. 16 ml (40 mmol) of 2.5 M of n-butyllithium in n-hexane. The solution was slowly warmed to room temperature and stirred for 3 hrs at room temperature (yellow brown suspension). Then to the suspension was added at −70° C. 13.4 g (35 mmol) of chloro-(2-i-propyl-4-(4-t-butylphenyl)-indenyl)-dimethylsilane and the solution was warmed to room temperature and stirred over the weekend. The resulting brown slurry solution was poured into an aqueous ammonium chloride solution and the organic layer was washed with brine, dried over sodium sulfate and the solvents were evaporated. The crude product was purified by column chromatography to get 17.0 g of amorphous solid (yield: 64%).

Provenance & Evidence