Sodium hydride promoted O-alkylation of 2-[(4-t-butyldimethylsilyloxy)phenyl]ethan-1-ol with 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene depend on the solvent used in the coupling reaction. Mixtures of 2-[4-(2-bromo-4,5-dimethoxybenzyloxy)phenyl]-1-t-butyldimethylsilyloxyethane and 2-[4-(2-bromo-4,5-dimethoxybenzyloxy)phenyl] ethan-1-ol (in DMF), or 2-[4-(2-bromo-4,5-dimethoxybenzyloxy)phenyl]-1-t-butyldimethylsilyloxyethane and 4-[2-(2-bromo-4,5-dimethoxybenzyloxy)ethyl]phenol (in THF), were detected. These results can be explained by an unusual intermolecular silyl migration reaction.
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11.
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