Chlorotrimethylsilane → [(Cyclooct-1-en-1-yl)oxy](trimethyl)silane

To a solution of 42 g (0.38 mol) of chlorotrimethylsilane and 78 g of triethylamine in 100 ml of dimethylformamide, a solution of 32 g (0.254 mol) of cyclooctanone in 40 ml of dimethylformamide was added. The resultant mixture was stirred at 100° to 115° C. for 48 hours. At the end of the reaction, the reaction mixture was combined with 240 ml of n-hexane and washed twice with 300 ml of a saturated aqueous sodium bicarbonate solution. The mixture was washed under cooling with 180 ml of 1.5N hydrochloric acid, then washed sequentially with an aqueous sodium bicarbonate solution, water, and saline and then dried with magnesium sulfate. The mixture was concentrated and distilled under vacuum, to afford 40 g (80% yield) of 1-cyclooctenyloxytrimethylsilane having a boiling point of 82° to 84° C./5 mmHg.

1. customAt the end of the reaction
2. washwashed twice with 300 ml of a saturated aqueous sodium bicarbonate solution
3. washThe mixture was washed
4. temperatureunder cooling with 180 ml of 1.5N hydrochloric acid
5. washwashed sequentially with an aqueous sodium bicarbonate solution, water, and saline
6. dry with materialdried with magnesium sulfate
7. concentrationThe mixture was concentrated
8. distillationdistilled under vacuum

ORD record

ord-f9c534ad4daf4b3aa7ad08960f36e0c6

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04849535