2,6-Lutidine → 5-Bromo-2-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridine

Participants

Reaction Steps

To a solution of 2-(5-bromopyridin-2-yl)propan-2-ol (1.20 g, 5.55 mmol, prepared according to the method in Tetrahedron Lett. 2000, 41, 4335) and 2,6-lutidine (1.29 mL, 11.11 mmol) in CH2Cl2 (12 mL) was added TBSOTf (1.91 mL, 8.33 mmol). After stirring at room temperature for 2 h, the reaction was diluted with water and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The crude residue was purified on silica gel (0-10% EtOAc/hexanes) which afforded the title compound as a colorless oil.

Provenance & Evidence