Potassium Carbonate → 5-(2H-1,2,3-Triazol-2-yl)indan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-1-indanone (5.0 g, 24 mmol) and 1H-triazole (4.90 g, 71.1 mmol) in 20 mL of DMF was added Fe(acac)3 (838 mg, 2.37 mmol), copper (II) oxide (188 mg, 2.36 mmol) and potassium carbonate (3.27 g, 23.7 mmol). The reaction mixture was degassed with nitrogen for 10 minutes. The mixture was stirred at 90° C. for 6.5 hours and at 80° C. for 15 hours. The cooled reaction mixture was diluted with ethyl acetate and water. The biphasic mixture was passed through a thin Celite® pad, which was washed thoroughly with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. Filtration and solvent removal afforded the crude product which was purified by silica chromatography using an ISCO (Teledyne Isco Inc., Lincoln Nebr.) column eluting with a 0-40% ethyl acetate/heptanes gradient to give the desired product as a pale yellow solid (2.60 g, 55%). MS (ES+) 200.1 (M+H)+. 1H NMR (CDCl3) δ 2.85 (t, 2H), 3.24 (t, 2H), 7.83-7.90 (m, 3H), 8.15 (d, 1H), 8.21 (s, 1H).

Provenance & Evidence