2,4,6-Trimethoxybenzaldehyde → (E)-2-methoxy-3-nitro-5-((2,4,6-trimethoxystyrylsulfinyl)methyl)pyridine

Participants

Reaction Steps

A solution of 2-((6-methoxy-5-nitropyridin-3-yl)methylsulfinyl)acetic acid (0.15 g, 0.5 mmol) in dry pyridine (20 mL) was treated with 2,4,6-trimethoxybenzaldehyde (0.20 g, 1 mmol) and piperidine (10 drops). The mixture was refluxed for 2-3 hrs. The mixture was evaporated and the residue was purified by flash chromatography; yield 10%; 1H-NMR (CDCl3): δ 3.83 (s, 6H, OCH3), 3.83 (s, 3H, OCH3), 3.89 (1H, CH), 4.07 (1H, CH), 4.09 (s, 3H, OCH3), 6.09 (s, 2H, Ph-H), 6.97 (d, 1H, J=15.2 Hz, CH), 7.28 (d, 1H, J=15.2 Hz, CH), 8.19 (d, 1H, J=2.3 Hz, Py-H), 8.29 (d, 1H, J=2.3 Hz, Py-H). HR-MS (ESI+) m/z 408.8426 C18H20N2O7S requires 408.0991.

Provenance & Evidence