Nitrogen → [5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-methanol

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-carboxylic acid methyl ester (10.0 g, 39.81 mmol) in THF (300.0 mL) was treated dropwise, at −78° C. with DiBAL (160.0 mL of a 1M solution in toluene, 160.0 mmol). The reaction mixture was stirred at −78° C. for 1.5 h and at rt for 1 h. Sat. aq. Rochelle's salt (600 mL) was added and the reaction mixture was stirred at rt for 1 h. The aq. layer was extracted with EA (2×350 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound. TLC: rf (40:60 hept-EA)=0.28. LC-MS-conditions 02: tR=0.74 min. 1H NMR (400 MHz, CDCl3) δ 2.10 (s, 1H), 4.62 (s, 2H), 5.31 (s, 2H), 6.33 (d, J=3.0 Hz, 1H), 6.47 (d, J=3.0 Hz, 1H), 8.08 (s, 1H), 8.15 (s, 1H).

Provenance & Evidence