Allylchlorodimethylsilane → tert-butyl-N-{4-[allyl(dimethyl)silyl]-2-ethoxyphenyl}carbamate

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Reaction Steps

The reaction between 5.3 g (16.8 mmol) of tert-butyl-N-(4-bromo-2-ethoxyphenyl)carbamate 5, 2.4 g (20.16 mmol, 1.2 eq) of 35% potassium hydride, 20.2 ml (34.4 mmol, 2.05 eq) of 1.5 M tert-butyllithium in hexane and 6 ml (40.3 mmol, 2.4 eq) of allyl(chloro)dimethylsilane according to the procedure described for compound 6, followed by two successive purifications by column chromatography (eluant petroleum ether/AcOEt 9:1), lead to 3.3 g of a colorless oil (yield: 58%).

Provenance & Evidence