3-Pyridinemethanol → Ethyl 2-((pyridin-3-yl)methoxy)acetate

Participants

Reaction Steps

(Step 4-i) Sodium hydride (60%) (0.44 g, 11 mmol) was added to a solution of (pyridin-3-yl)methanol (1.09 g, 10 mmol) in THF. The reaction mixture was stirred at room temperature for 10 min and ethyl bromoacetate (1.8 g, 11 mmol) was added, followed by the addition of 20 mg of tetrabutyl ammonium iodide. The reaction mixture was stirred overnight, diluted with ethyl acetate/saturated sodium bicarbonate, and the organic layer was dried over sodium sulfate. The solution was concentrated to an oil, which was purified by silica gel column chromatography to give the product, ethyl 2-((pyridin-3-yl)methoxy)acetate, as a brown oil (0.63 g, 3.2 mmol, 32% yield): 1H-NMR (500 MHz, DMSO-d6) 8.63 (d, J=1.8 Hz, 1H), 8.59 (dd, J=1.5, 4.8 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.34 (dd, J=4.9, 7.7 Hz, 1H), 4.68 (s, 2H), 4.26 (q, J=7.1 Hz, 2H), 4.15 (s, 2H), 1.32 (t, J=7.1 Hz, 3H).

Provenance & Evidence