Sodium hydride → HCID 67190155, compound

Participants

Reaction Steps

To a solution of 3-nitro-1H-pyrazole (prepared in example 3, 200 mg, 1.77 mmol) in anhydrous N,N-dimethylformamide (2 mL), a 60% dispersion of sodium hydride in mineral oil (92 mg, 2.30 mmol) was added while stirring under nitrogen. After the effervescence ceased and the mixture was stirred for additional 20 min, 4-methyoxybenzylchloride (312 μL, 2.30 mmol) was added. The mixture was continued to stir under nitrogen for an additional 2 h. The solvent was removed in vacuo and purification by ISCO flash column chromatography (Teledyne Isco RediSep Flash Column 40 g; 2% methanol/methylene chloride to 5% methanol/methylene chloride) afforded 1-(4-methoxy-benzyl)-3-nitro-1H-pyrazole (337 mg, 82%) as a white solid: H1-NMR (400 MHz, CDCl3) δ: 3.77 (3H, s), 5.27 (2H, s), 6.83 (1H, d, J=2.3 Hz), 6.86 (2H, d, J=8.6 Hz), 7.22 (2H, d, J=8.5 Hz), 7.35 (1H, d, J=2.3 Hz).

Provenance & Evidence