Acetic Acid → HCID 67486594, compound

Participants

Reaction Conditions

Reaction Steps

NaOEt (0.63 mL of a 0.5M solution in EtOH, 0.32 mmol) was added dropwise to a stirred solution of ethyl(4-[1,2,3]triazol-1-ylphenyl)acetate (730 mg, 3.16 mmol) and tetrahydropyran-4-carboxaldehyde (396 mg, 3.47 mmol) in anhydrous DMSO (3 mL). The mixture was heated at 80° C. for 16 h, before being treated with AcOH to adjust the pH to 7. EtOAc (30 mL) was added, then the solution was washed with H2O (2×10 mL) and brine (10 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 1:1) yielded ethyl 3-(tetrahydropyran-4-yl)-2(4-[1,2,3]triazol-1-ylphenyl)acrylate: m/z (ES+)=328.2 [M+H]+. This ester (404 mg, 1.23 mmol) was saponified as described above in Preparation 25 to give the title compound: m/z (ES+)=300.2 [M+H]+.

Provenance & Evidence