Triethylamine → [(3-Bromonaphthalen-1-yl)methoxy](tert-butyl)dimethylsilane

Participants

Reaction Steps

To a solution of 1.49 g (6.3 mmoles) of 3-bromo-1-(hydroxymethyl)-naphthalene in 25 ml anhydrous CH2Cl2 were added sequentially N,N-dimethyl-4-aminopyridine (76.8 mg, 0.63 mmoles), t-butyldimethylchlorosilane (1.23 g, 8.2 mmoles) and triethylamine (1.22 ml, 8.8 mmoles). The resulting solution was stirred at room temperature for 2 hours under a N2 atmosphere and then partitioned between EtOAc and ice/H2O. The organic phase was separated, washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under vacuum to provide a pale yellow liquid. The crude reaction residue was purified by column chromatography (44 g silica gel, packed and eluted with 9:1 hexanes: CH2Cl2) to provide 2.19 g of the title compound as a clear liquid.

Provenance & Evidence