Toluene → Ethyldimethyl(((1SR,4RS)-3-methylbicyclo[2.2.1]hept-2-en-2-yl)methyl)silane

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Triethyl aluminium (1.0 M in hexanes, 4.2 mL, 4.2 mmol) was added slowly dropwise to a suspension of Ni(acac)2 (dried in vacuo 120° C. 3 hrs, 107 mg, 0.4 mmol, 5 mol %), santadiene (1.0 g, 8.3 mmol) in freshly degassed toluene (85 mL) cooled to 0° C. After 15 minutes, dimethyl ethyl silane (1.1 mL, 8.3 mmol) was added slowly dropwise and the solution was then allowed to slowly warm to ambient temperature and stirred for a further 2 hours. The reaction mixture was poured into saturated ammonium chloride solution and extracted with ether, then the combined organic phase was washed with brine and dried over Na2SO4, then filtered and the solvents removed in vacuo to yield the crude allyl silane 0.9 g, which was further purified by bulb to bulb distillation 30° C. at 0.08 mbar and gave the desired ally silane 0.65 g, 37%.

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