3-Furanol, tetrahydro- → HCID 86679660, compound

Participants

Reaction Steps

To a solution of 4-nitropyrazole (1 g, 8.8 mmol), 3-hydroxy-tetrahydrofuran (779 mg, 8.8 mmol) and triphenylphosphine (2.81 g, 10.56 mmol) in THF (30 mL) at 0° C. was added diisopropylazodicarboxylate (2.27 g, 1 mmol) dropwise and the reaction was allowed to warm to rt overnight. The reaction was concentrated and purified on SiO2 (30% EtOAc/heptane) to give 4-nitro-1-(tetrahydrofuran-3-yl)-1H-pyrazole as a clear oil. The oil was then dissolved in EtOH (30 mL) and hydrogenated via H-cube with 10% Pd/C at 30 psi H2 for 3 hrs. The solvent was removed and the residue was purified on SiO2 (1%-10% EtOH/EtOAc) to give the title compound (1.0 g, 42% yield) as an orange oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.10-2.21 (m, 1H), 2.22-2.35 (m, 1H), 3.72-3.85 (m, 4H), 3.85-3.96 (m, 2H), 4.76-4.85 (m, 1H), 6.93 (s, 1H), 7.05 (s, 1H). m/z (APCI+) for C7H11N3O 154.1 (M+H)+.

Provenance & Evidence