Hydrogen Peroxide → 4-Pentyl-4-phenyl-4-silacyclohexanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 15.9 g of 9-borabicyclo [3.3.1] nonan, 14.8 g of n-pentylphenyldivinylsilane and 150 ml of n-hexane was refluxed for 2 hours and then cooled with ice water. 7.0 ml of borane-dimethylsufide was added to the mixture, which was then heated again and refluxed for 2 hours. After cooling, 16 ml of methanol was added at room temperature and the mixture was stirred for 2 hours at 0° C. 25.0 g of dichloromethylmethyl ether was then dripped into the mixture, followed by also dripping a hexane-tetrahydrofuran (1:1) solution of 1.33M lithium t-butoxide into the mixture. After stirring at room temperature for 2 hours, 80 ml of ethanol, 10 ml of water and 10.0 g of sodium hydroxide were added. Then 80 ml of an aqueous solution of 30% hydrogen peroxide was slowly added. After stirring at room temperature for 2 hours, the organic layer was dried/concentrated to obtain a mixture of the target product and bicyclo [3.3.1] nonan-9-one. They were separated by means of silica-gel chromatography to obtain 15.2 g (yield 91%) of the target product. The target product thus obtained exhibited the same spectra as those of Example 7.

Provenance & Evidence