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

Temperature

0 °C

To a 20 ml THF solution of 7 ml of N,N-diisopropylamine, 35.4 ml of a 1.4M n-butyl lithium solution was added dropwise at −78° C., followed by stirring at 0° C. for 30 minutes. The resulting diisopropylamino lithium (LDA) solution was then added dropwise to a 10 ml THF solution of 4 ml of 4-methylcyclohexan-1-one at −78° C. After stirring at −78° C. for 1 hour, 6.5 ml of trimethylsilyl chloride was added dropwise. After stirring at room temperature for 1 hour, the reaction mixture was poured into an aqueous sodium bicarbonate solution. The resulting mixture was extracted with ether. The organic layer was washed with saturated saline, dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. Distillation under reduced pressure yielded 5.83 g of 4-methyl-1-(trimethylsilyloxy)-1-cyclohexene (yield: 96%).

1. stirringAfter stirring at −78° C. for 1 hour
2. stirringAfter stirring at room temperature for 1 hour
3. extractionThe resulting mixture was extracted with ether
4. washThe organic layer was washed with saturated saline
5. dry with materialdried over magnesium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent
8. distillationDistillation under reduced pressure

ORD record

ord-59ff2e53e5274264a9396bfc36897456

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06906107B2