Nitrogen → 5-(3-Nitro-pyrazol-1-ylmethyl)-furan-2-carbaldehyde

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(3-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol (13.80 g, 61.83 mmol) in AcCN (631.0 mL) was treated at rt with MnO2 (35.84 g, 370.98 mmol). The reaction mixture was stirred at rt for 16 h before being filtered through Celite and the solvent was removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound. TLC: rf (60:40 hept-EA)=0.16. LC-MS-conditions 02: tR=0.81 min. 1H NMR (400 MHz, CDCl3) δ 5.48 (s, 2H), 6.67 (d, J=3.5 Hz, 1H), 6.96 (d, J=2.5 Hz, 1H), 7.24 (d, J=3.8 Hz, 1H), 7.64 (d, J=2.5 Hz, 1H), 9.65 (s, 1H).

Provenance & Evidence