Phenylacetylene → 1,5-Diphenyl-1H-1,2,3-triazole

Participants

Reaction Conditions

Reaction Steps

To a solution of EtMgBr in THF (1.0M, 11.9 mL) was added phenylacetylene (1.30 mL, 11.9 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 min. After cooling the mixture to room temperature, a solution of phenylazide (1.41 g, 11.9 mmol) in THF (4 mL) was added. The resulting solution was stirred at room temperature for 30 min, and then heated to 50° C. for 1 hour before quenching with saturated NH4Cl (10 mL). The layers was separated, and the aqueous layer was extracted with CH2Cl2 (10 mL×3). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the 1,5-diphenyltriazole as a white solid (1.98 g, 75%). 1H NMR (CDCl3, 300 MHz) δ 7.86 (s, 1H), 7.44-7.30 (m, 8H), 7.23-7.20 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 137.6, 136.5, 133.4, 129.3, 129.2, 128.8, 128.5, 126.7, 125.1.

Provenance & Evidence