3-Hydroxypyridine → Methyl 2-(pyridin-3-yloxy)acetate

Participants

Reaction Steps

To a solution of 3-hydroxypyridine(5 g) in DMF(50 ml) was added slowly sodium hydride(2.1 g) under ice cooling. After the addition was completed, the reaction mixture was warmed up to room temperature and stirred at the same temperature for 30 minutes. The mixture was cooled with ice and methyl bromoacetate (8.1 g) was added slowly. After the addition was completed, the reaction mixture was stirred at room temperature for 15 hours and poured into ice water. The product was extracted with ethyl acetate, washed with brine, dried(MgSO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel (chloroform: methanol=20:3) to obtain methyl 2-(3-pyridyloxy)acetate(1.7 g).

Provenance & Evidence