Chlorotrimethylsilane → [(Bicyclo[2.2.1]hept-2-en-2-yl)oxy](trimethyl)silane

Participants

Reaction Conditions

Reaction Steps

Methyllithium in diethyl ether (141 ml of 1.8 M solution) was added dropwise to a solution of 27.6 g of diisopropylamine in 38 ml of dry diethyl ether. The resulting solution was cooled to -78° C. and 19.7 g of norcamphor in 20 ml of diethyl ether were added dropwise. The reaction mixture was warmed to 0° C. and 46 ml of chlorotrimethylsilane were added. The reaction mixture was warmed to 25° C., stirred for 30 minutes, extracted with cold 5% aqueous sodium bicarbonate, dried (over MgSO4) and then distilled to give 22.3 g of 2-trimethylsiloxybicyclo[2.2.1]-hept-2-ene as a colorless liquid: bp 70°-73° C. (14 mm).

Provenance & Evidence