Water → HCID 45095564, compound

Participants

Reaction Steps

A mixture of 3-(3-dimethoxymethyl-1-ethyl-1H-pyrazol-5-yl)-benzonitrile (5.0 g, 18.4 mmol), TFA (5.0 mL), H2O (20 mL) and THF (50 mL) was stirred at RT for 1 hour and then concentrated under reduced pressure to remove the organic solvents. The residue was neutralised with 1N NaOH solution (100 mL), extracted with EtOAc (2×150 mL), dried (MgSO4) and concentrated under reduced pressure while dry loading onto MgSO4. The mixture was then purified by column chromatography on silica eluting with 35-60% EtOAc/iso-hexanes to yield the desired aldehyde (2.91 g, 70%). 1H NMR (CDCl3, 500 MHz) δ 10.00 (1H, s), 7.80-7.72 (1H, m), 7.70 (1H, s), 7.67-7.60 (2H, m), 6.84 (1H, s), 4.23 (2H, q, J=7.3 Hz), 1.49 (3H, t, J=7.3 Hz). MS (ES+) C13H11N3O requires: 225, found: 226 (M+H+, 100%).

Provenance & Evidence