Tetrahydrofuran → (Z)-methyl 4-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-(4-chloro-2-methylphenyl)but-3-enoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-2-(4-chloro-2-methylphenyl)acetaldehyde (13 g, 36.1 mmol) in THF (200 mL) was added methyl (triphenylphosphoranylidene)acetate (24.13 g, 72.2 mmol). The mixture was stirred at about 60° C. for about 16 h then cooled in an ice bath. The solids were removed by filtration then filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, 0-20% EtOAc/heptanes) to give (Z)-methyl 4-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-(4-chloro-2-methylphenyl)but-3-enoate (13.34 g, 89%): LC-MS (Table 1, Method g) Rt=2.62 min, m/z 416/418 (M+H)+; 1H-NMR (DMSO, Bruker 400 MHz) δ 8.41-8.38 (m, 1H), 7.81-7.70 (m, 2H), 7.27-7.20 (m, 1H), 7.19-7.17 (m, 1H), 7.09-7.05 (m, 1H), 7.02-6.99 (m, 1H), 5.91 (t, J=7.3 Hz, 1H), 3.91 (s, 3H), 3.52 (s, 3H), 3.11-2.96 (m, 2H), 2.34 (s, 3H).

Provenance & Evidence