Water → 1-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

BuLi (10.6 mL, 1.6 M in hexane, 17.0 mmol) was added dropwise to at solution of 1-methyl-3-phenyl-1H-1,2,4-triazole (2.7 g, 17.0 mmol) in THF (85 mL) at −78° C. The mixture was warmed to −40° C. over 15 min and recooled to −78° C. DMF (1.32 mL, 17 mmol) was added dropwise and the mixture was warmed to ambient temperature over 2 h. Water was added to the mixture and it was extracted with EtOAc (3×). The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (EtOAc, hexanes) yielded 2.75 g of Intermediate 386.1 as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.22 (s, 3H) 7.34-7.56 (m, 3H) 8.10 (dd, J=7.58, 1.71 Hz, 2H) 10.03 (s, 1H).

Provenance & Evidence