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

Temperatur

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 diisopropyl aminolithium (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-Eintrag

ord-7f6549552bd543cfb5a312dae9693b09

Quelldatensatz

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07838565B2