Acetic Anhydride → Acetic Acid 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-yl Ester

Participants

Reaction Steps

Acetanhydride (0.26 ml) was added dropwise into a solution of 100 mg of 6-(5-nitropyridin-2-yloxy)-2-phenylchroman-4-ol (Example 8(b)) in dry pyridine. The reaction mixture was refluxed for 1½ hours. It was then poured in ice-water and extracted with ethyl acetate. The organic phase was washed with 1 M HCl-solution, water and saturated NaCl-solution. It was then dried with MgSO4 and evaporated to dryness. 1H NMR (400 MHz, d6-DMSO) δ: 9.05 (d, 1H, J 2.8 Hz), 8.61 (dd, 1H, J 9.1, 2.8 Hz), 7.52-7.35 (m, 5H), 7.23 (d, 1H, J 9.1 Hz), 7.14-7.10 (m, 2H), 6.98 (d, 1H, J 8.5 Hz), 6.18 (dd, 1H, J 10.1, 6.4 Hz), 5.44(dd, 1H, J 11.4, 1.4Hz), 2.51 (m, 1H), 2.15 (m, 1H), 2.05 (s, 3H).

Provenance & Evidence