Triethylamine → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-pyridylcarbinol (50.3 g, 0.46 mol) in methylene chloride (250 mL) under a dry nitrogen atmosphere was added triethylamine (97 mL, 0.69 mol). To this mixture was added dropwise tert-butyl-dimethylsilyl chloride (83.7 g, 0.555 mol) with cooling (T 34° C.). The reaction mixture was stirred overnight at room temperature. The slurry was then filtered and the solvent removed by rotoevaporation. The residue was suspended in toluene and filtered and the solvent removed by rotoevaporation. The residue was suspended in diethyl ether and filtered and the solvent removed by rotoevaporation. The same process was repeated with hexanes to yield 4-t-butydimethylsilyloxymethylpyridine as a brown oil.

Provenance & Evidence