1-Pentyne → 4-(4-propyl-1H-1,2,3-triazol-1-yl)pyridine

Participants

Reaction Steps

4-azidopyridine (4.65 g, 38.7 mmol) and pent-1-yne (4.12 ml, 41.8 mmol) were added into a 250 mL round-bottom flask with 50 mL mixture of water/acetone. Copper(II) sulfate (0.060 g, 0.376 mmol) and sodium L-ascorbate (0.256 g, 1.292 mmol) were added to this solution and the reaction was stirred at room temperature for 24 hours. Additional sodium ascorbate (0.103 g) was added. The solution was filtered and concentrated. Ethyl acetate (200 ml) was added to the concentrated solution. The organic layer was washed twice with 25 mL water, dried with MgSO4, filtered, concentrated and dried in vacuo, producing 4-(4-propyl-1H-1,2,3-triazol-1-yl)pyridine.

Provenance & Evidence