Acetic Anhydride → HCID 25228380, compound

Participants

Reaction Steps

Referring to FIG. 20, under a nitrogen atmosphere, DMAP (0.0102 g) and acetic anhydride (0.015 mL, 0.158 mmol) were added to a solution of 10b (0.0090 g, 0.0369 mmol) in chloroform (5 mL) and pyridine (1.5 mL). The reaction was stirred for 24 h. The solvents were evaporated, and the remaining residue was purified by column chromatography (3:7 EtOAc/hexane) to provide 11b (0.0100 g, 0.0351 mmol, 95% yield) as a white solid: 1H NMR (CDCl3) δ 8.16 (1H, d, J=8.0 Hz), 7.98 (1H, d, J=9.2 Hz), 7.55 (1H, d, J=9.2 Hz), 7.44 (1H, d, J=8.4 Hz), 5.46 (2H, s), 5.45 (2H, s), 3.58 (3H, s), 2.26 (3H, s); 13C NMR (CDCl3) δ 170.7, 162.2, 159.2, 148.2, 136.9, 133.5, 122.7, 118.5, 115.7, 114.5, 95.1, 66.7, 56.9, 21.0; FTIR (neat) 2924, 2342, 2224, 1738, 1612, 1508, 1246, 1157, 1070, 937, 846 cm−1; MS (ESI) m/z calculated for (C15H14N2O4+H)+ 287, found 287; HRMS (ESI) m/z calculated for (C15H14N2O4+H)+ 287.1033, found 287.1059.

Provenance & Evidence