Nitroethane → HCID 58481173, compound

Participants

Reaction Steps

To diethyl 2-acetamido-2-(4-fluoro-3-nitrobenzyl)malonate (7.41 g) and nitroethane (6.0 mL) in EtOAc was added DBU (9.0 mL) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was dissolved in methanol (35 mL). Aqueous H2O2 (30%, 10.2 mL) and 10% aqueous NaHCO3 (10.2 mL) were added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with 1 N HCl, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (10-20% EtOAc in DCM), affording diethyl 2-acetamido-2-(4-acetyl-3-nitrobenzyl)malonate. 1H NMR (400 MHz, MeOD): δ 7.73 (s, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 4.25 (q, J=7.2 Hz, 4H), 3.72 (s, 2H), 2.53 (s, 3H), 2.03 (s, 3H), 1.28 (t, J=7.2 Hz, 6H); 13C NMR: δ 172.99, 168.22, 153.68, 147.48, 140.96, 137.31, 136.82, 128.99, 126.79, 68.62, 63.95, 54.01, 38.58, 22.32, 14.36; ESI-MS (m/z) 395.38(MH+).

Provenance & Evidence