((2-Bromo-5-methoxybenzyl)oxy)(tert-butyl)dimethylsilane → 2-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1-ethenyl-4-methoxybenzene

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Reaction Steps

Under a nitrogen atmosphere, 33.63 9 (0.10 mol) of (2-bromo-5-methoxy-benzyloxy)-tert-butyl-dimethyl-silane (14), 32.18 9 (0.10 mol) of tributylvinyl tin and 4.7 g (0.004 mol) of tetrakis(triphenylphosphine)palladium(0) were combined in 250 mL of toluene, and the solution was heated to reflux for 6 hours. The reaction was allowed to cool to ambient temperature and was quenched with 5% NH4OH (2×100 mL). The organic layer was washed with water (1×200 mL) and brine (1×200 mL), dried over sodium sulfate, filtered and concentrated in vacuo to yield crude product. The crude product was chromatographed on a silica gel column, first with hexane, then with 20% CHCl3 in hexane, and finally with 40% CHCl3 in hexane to afford 25.0 9 (89%) of tert-butyl-dimethyl-(2-vinyl-5-methoxy-benzyloxy)-silane (15).

Provenance & Evidence