Water → 4-(Tert-butyldimethylsilyloxyethyl)-pyridine

Participants

Reaction Steps

Commercially available 4-(2-hydroxyethyl)pyridine (10.0 g, 81.2 mmol) was dissolved in dichloromethane (400 mL), then 2,6-lutidine (26.1 g, 244 mmol) and chloro-tert-butyldimethylsilane (32.0 g, 121 mmol) were added thereto, followed by stirring at room temperature for 3 hours. After completion of the reaction was confirmed by thin-layer chromatography, water was added to the reaction mixture, and the resulting mixture was separated into organic layer and aqueous layer. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure to give 4-[2-(tert-butyldimethylsiloxy)ethyl]pyridine (19.2 g, quantitative yield).

Provenance & Evidence