Hydrazine hydrate (1:1) → HCID 18406882, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-3-phenyl-2-furanone (5 g, 28.3 mmol) was dissolved in EtOH (60 mL) with hydrazine hydrate (6.9 mL, 0.142 mol) and heated at 140° C. in a sealed tube for 64h. Further hydrazine hydrate (4 mL, 82 mmol) was added and the mixture heated at 140° C. for another 48h. The solvent was evaporated and the residue was chromatographed on silica, eluting with 10% MeOH/DCM, followed by 20% MeOH/DCM to afford the title compound (3.62 g, 67%) as a cream solid. mp 165-168° C. 1H NMR (400 MHz, d6-DMSO) δ4.45 (2H, d, J=5.0 Hz), 5.30 (1H, t, J=5.0 Hz), 7.15 (1H, t, J=7.4 Hz), 7.33 (2H, t, J=7.6 Hz), 7.55 (2H, d, J=7.7 Hz), 9.90 (1H, brs), 11.75 (1H, brs).

Provenance & Evidence