Water → HCID 136350251, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (20 mg, 0.07 mmol), hydroxylamine hydrochloride (93.8 mg, 1.35 mmol) and pyridine (164 μL, 2.02 mmol) in dry EtOH (1.6 mL) was heated at 120° C. for 15 minutes in the microwave. Water and DCM were added and the phases were separated. The crude product was purified on preparative HPLC to give 4-(2,4-dimethylfuran-3-yl)-3-(4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde oxime (6.2 mg, 30%). Identification of the title compound by 1H-NMR showed that the oxime product was a single isomer, but did not confirm whether the (E) or (Z) oxime isomer had been obtained. ES/MS m/z: 312.1 (M+H), 310.26 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.77 (s, 1H), 7.40 (m, 2H), 7.32 (q, 1H, J=1.0 Hz), 6.76 (m, 2H), 4.09 (s, 3H), 2.02 (s, 3H) and 1.63 (q, 3H, J=1.0 Hz).

Provenance & Evidence