Triethylamine → [(3-Bromophenanthren-9-YL)methoxy](tert-butyl)dimethylsilane

Participants

Reaction Steps

To a solution of 3-bromo-9-(hydroxymethyl) phenanthrene, 4 (5.96 g, 20.8 mmol) and t-butyldimethylsilyl chloride (4.7 g, 31 mmol) in 100 ml of CH2Cl2 and 20 ml of THF was added triethylamine (4.9 ml, 35 mmol) followed by 4-methylaminopyridine (250 mg, 2.05 mmol). After stirring at room temperature for 20 hours, the solution was poured into 300 ml of ethyl ether and washed successively with sat. NH4Cl, sat. NaHCO3, H2O, and brine. Drying (Na2SO4) and evaporation gave a brown solid which was purified by flash chromatography through 400 g of silica gel (1:4 CH2Cl2 -hexane) to yield 7.23 g (87%) of the title compound as a pale yellow solid.

Provenance & Evidence