Triphenylphosphine → Methyl 5-(but-2-yn-1-yloxy)picolinate

Participants

Reaction Steps

To a solution of but-2-yn-1-ol (0.635 mL, 8.49 mmol) in THF (30 mL) were added methyl 5-hydroxypicolinate (1.3 g, 8.49 mmol), triphenylphosphine (3.34 g, 12.73 mmol) and diisopropyl azodicarboxylate (2.507 mL, 12.73 mmol) at 0° C. The reaction mixture was then allowed to reach r.t and stirred for 2 days. The reaction mixture was concentrated and the product was purified by flash chromatography using a heptane/EtOAc gradient to give 1.42 g (82% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.87 (t, 3 H), 4.00 (s, 3 H), 4.79 (q, 2 H), 7.41 (dd, 1 H), 8.11-8.20 (m, 1 H), 8.49 (d, 1 H).

Provenance & Evidence