Ammonium formate → HCID 59356083, compound

Participants

Reaction Steps

Compound 41 was prepared following the general procedure described by Wähälä and Hase, Heterocycles 1989, 28, (1), 183-186, herein incorporated by reference. To a 10 mL round bottom flask was added 2′-chloroisoflavone (152 mg, 0.592 mmol) and ammonium formate (149 mg, 2.37 mmol). The flask was purged with N2, followed by addition of methanol (8 mL) and 10% Pd/C (151 mg). The reaction was allowed to stir at room temperature and monitored by reverse phase HPLC. Upon consumption of starting material, the reaction mixture was passed through a pad of silica gel using EtOAc as the eluent. The solvent was concentrated in vacuo to afford crude 41. Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford 41 (21 mg, 14%) as an off-white solid. Analytical data for isoflavanone 41: 1H NMR (500 MHz, CDCl3) δ 7.98 (d, J=9.5 Hz, 1H), 7.53 (app t, J=9 Hz, 1H), 7.39-7.28 (m, 4H), 7.09-7.03 (m, 2H), 4.71-4.66 (m, 2H), 4.04-4.01 (app t, J=6.5 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 192.4, 161.8, 136.3, 133.2, 129.1, 128.9, 128.1, 128.0, 121.9, 121.3, 118.1, 71.7, 52.6; GCMS: Mass calculated for C15H11ClO2, [M]+, 259. Found 225.

Provenance & Evidence