Water → HCID 59648601, compound

Participants

Reaction Steps

To 5-(2-azido-3-ethoxy-3-oxoprop-1-enyl)furan-2-carboxylic acid (0.50 g, 2.03 mmol) was added a mixture of NaHCO3 (0.34 g, 4.06 mmol) and Selectfluor® (1.08 g, 3.05 mmol), followed by water (4.0 mL), hexane (5.0 mL) and EtOAc (2.0 mL). The mixture was stirred at rt for 5 min. The organic layer was separated, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (0 to 30% EtOAc in heptane over 20 min) yielded pure ethyl 2-azido-3-(5-fluorofuran-2-yl)prop-2-enoate as a reddish oil (0.20 g, 45%). 1H NMR (400 MHz, CD3OD) δ ppm 1.35 (t, J=7.15 Hz, 3H) 4.32 (q, J=7.16 Hz, 2H) 5.74 (dd, J=6.83, 3.66 Hz, 1H) 6.63 (s, 1H) 7.05 (t, J=3.59 Hz, 1H). 19F NMR (376 MHz, CD3OD) δ ppm −115.12 (dd, J=6.60, 3.30 Hz).

Provenance & Evidence