3-Hydroxypyridine → Tert-butyl 2-(3-pyridyloxy)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of t-butyl bromoacetate (2 g, 10 mmol), 3-hydroxypyridine (1.5 g, 15 mmol), and K2CO3 (2.9 g, 21 mmol) in THF (20 mL) is stirred at 60° C. After 0.5 h, the reaction mixture is cooled down at room temperature and diluted with H2O, then extracted with EtOAc. The organic phase is washed with H2O, and brine, then dried over Na2SO4. The solution is filtered and the solvent is evaporated in vacuo. The residue is purified by silica gel column chromatography to give the title compound MS: 210 [M+H]+; tR (HPLC, ACQUITY UPLC™ BEH C18 1.7 μm, 50×2.1 mm; 5% CH3CN+0.1% TFA/H2O+0.1% TFA for 0.5 min then 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 1.5 min, flow 0.5 ml/min): 1.85 min.

Provenance & Evidence