Chlorotrimethylsilane → HCID 11063095, compound

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, a solution of 2-methylcyclohexanone (0.5 g, 4.46 mmol) in anhydrous tetrahydrofuran (1 mL) was added dropwise to a solution of lithium diisopropylamide 2.0M in tetrahydrofuran (2.45 mL, 4.90 mmol) in anhydrous tetrahydrofuran (10 mL), previously cooled at −78° C. After stirring for 30 minutes at the same temperature, trimethylsilyl chloride (0.96 mL, 7.58 mmol) was added and the reaction mixture was stirred at room temperature for 1 hour before being quenched with a saturated solution of ammonium chloride (10 mL) at 0° C. Diethyl ether (20 mL) was added and the mixture was allowed to reach room temperature. Layers were separated and the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane) to provide trimethyl[(6-methylcyclohex-1-en-1-yl)oxy]silane (18a) (660 mg, 3.58 mmol, 80%)

Provenance & Evidence