3,5-Dimethylpyrazole → HCID 69748164, compound

Participants

Reaction Steps

To a stirring solution of 4-[Chloro-(3-methoxy-phenyl)-methyl]-benzoic acid methyl ester (5.0 g, 17.3 mmol) in 87 mL CH3CN was added 3,5-dimethyl pyrazole (5.0 g, 51.8 mmol) and tetra-n-butyl ammonium iodide (3.2 g, 8.6 mmol). The mixture was heated to reflux for 24 h, cooled to room temperature and concentrated under reduce pressure. The crude oil was purified by flash chromatography with 30% ethyl acetate/hexanes, collecting 8 mL fractions. The product containing fractions were collected and concentrated under reduce pressure to give the desired product (1.8 g, 30%) as a clear yellow oil. 400 MHz 1H NMR (CDCl3) δ 7.97 (d, J=8.5 Hz, 2H), 7.19-7.25 (m, 3H), 6.81-6.83 (m, 1H), 6.68-6.73 (m, 2H), 6.52 (s, 1H), 5.85 (s, 1H), 3.89 (s, 3H), 3.72 (s, 3H), 2.20 (s, 3H), 2.16 (s, 3H); MS (M+1) 351.2.

Provenance & Evidence