Chlorotrimethylsilane → 4-Methyl-1-(trimethylsilyloxy)-1-cyclohexene

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A 1.4M n-butyllithium solution (35.4 ml) was added dropwise to a solution of 7 ml of N,N-diisopropylamine in 20 ml of THF at −78° C. The resulting mixture was stirred at 0° C. for 30 min. Four ml of 4-methylcyclohexan-1-one in 10 ml of THF at −78° C. was added dropwise to the LDA solution. After stirring at −78° C. for 1 hour, 6.5 ml of trimethylsilyl chloride were added to the reaction mixture. The resulting mixture was stirred at room temperature for 1 hour and then poured into an aqueous solution of sodium bicarbonate, followed by extraction with ethyl ether. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by distillation under reduced pressure, whereby 5.83 g of 4-methyl-1-(trimethylsilyloxy)-1-cyclohexene were obtained. Yield: 96% TLC:(hexane-AcOET:8-2)Rf=0.8

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