2-ACETYL-5-NITROFURAN synthesis

Yield:5275-69-4 94%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane; for 1 h;Inert atmosphere;

Steps:

1-(5-Nitrofuran-2-yl)ethan-1-one (36):

Dess-Martin periodinane (8.62 g, 20.4 mmol) was added to 1-(5-nitrofuran-2-yl)ethan-1-ol (3.20 g, 20.4 mmol) dissolved in CH2Cl2 (250 mL), and the reaction mixture was stirred for 1 h. The reaction was quenched with saturated solutions of sodium thiosulfate and NaHCO3, then extracted with CH2Cl2 (3 x 50 mL), which was washed with water and brine, dried with Na2SO4, and evaporated under reduced pressure. Flash chromatography of the crude product using a prepacked 100 g silica column [eluents: solvent A, EtOAc; solvent B, hexanes; gradient, 7% A/93% B over 1.19 min (1 CV), 7% A/93% B 50% A/50% B over 13.12 min (10 CV), 50% A/50% B over 2.38 min (2 CV); flow rate 100.0 mL/min; monitored at 254 and 280 nm] yielded 1-(5-nitrofuran-2-yl)ethan-1-one (36) (2.98 g, 19.2 mmol, 94%) as yellow solid.1H NMR (600 MHz, CDCl3) δ 7.38 (1H, d, J = 3.8 Hz), 7.28 (1H, d, J = 3.7 Hz), 2.61 (3H, s).13C NMR (151 MHz, CDCl3) δ 186.73, 151.91, 151.48, 116.79, 111.94, 26.27.

References:

Winn, Blake A.;Shi, Zhe;Carlson, Graham J.;Wang, Yifan;Nguyen, Benson L.;Kelly, Evan M.;Ross, R. David;Hamel, Ernest;Chaplin, David J.;Trawick, Mary L.;Pinney, Kevin G. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 3,p. 636 - 641] Location in patent:supporting information