m-Chloroperbenzoic acid → HCID 67711257, compound

Participants

Reaction Steps

2-(E-2-Carboxymethylethenyl)-3-dodecyloxy-6-methylpyridine (2.15 g, 5.95 mmol) was dissolved in dry CH2Cl2 (20 mL) and cooled to 0∞C.; 85% m-chloroperoxybenzoic acid (1.45 g, 7.14 mmol) was added and the reaction was stirred at 0∞C. for 30 minutes and at room temperature for 16 hours. The reaction solution was poured into saturated aqueous NaHCO3 (20 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the combined CH2Cl2 extracts were washed with H2O (20 mL) and brine and dried (MgSO4). The crude pale yellow solid was used directly in the next step without further purification: 1H NMR (250 MHz, CDCl3): δ8.23 (d, J=16.2 Hz, 1H, olefin), 7.58 (d, J=16.2 Hz, 1H, olefin), 7.13 (d, J=8.8 Hz, 1H, 5-pyridyl), 6.79 (d, J=8.8 Hz, 1H, 4-pyridyl), 4.06 (t, J=6.6 Hz, 2H, OCH2), 3.81 (s, 3H, CO2CH3), 2.45 (s, 3H, CH3), 1.92-0.85 (m, 23H, aliphatic); MS (CI): 378.2 (M+H).

Provenance & Evidence