Acetic Anhydride → N-Acetyl-2-(2-Penylchroman-6-yloxy)-aniline

Participants

Reaction Steps

2-(2-Penylchroman-6-yloxy)-aniline (0.093 g) was dissolved in 1 ml of dry pyridine under nitrogen. DMAP (10 mol-%) and acetic acid anhydride (0.1 ml) were added and the solution was stirred for 4 hours at room temperature followed with quenching with 0.5 ml of H2O. The solution was evaporated to dryness and toluene was added and evaporated again. Toluene evaporation was repeated. Product was purified by column chromatography (CH2Cl2:i-PrOH/98:2 as the eluant) and recrystallized from 0.5 ml of heated absolute ethanol by cooling and adding 0.5 ml of 1H-NMR (400 MHz; d6-DMSO): δ 9.43 (s, 1H), 7.96 (m, 1H), 7.48-7.30 (m, 5H), 7.08-6.99 (m, 2H), 6.89-6.74 (m, 4H), 5.10 (dd, 1H, J=9.9, J=2.0), 3.03-2.88 (m, 1H), 2.76-2.65 (m, 1H), 2.21-2.11 (m, 1H), 2.10-1.91 (m, 1H), 2.06 (s, 3H).

Provenance & Evidence