(4,5-Dimethoxy-2-nitrophenyl)-(5-methylfuran-2-yl)methanone

To continue our investigation into the chemistry of furan derivatives [1, 2], we have synthesized furylphenylketone bearing nitro-group in the ortho-position of benzene ring. We developed reaction conditions for preparation of this compound smoothly and in rather high yield.

To an ice-cooled solution of ketone 1 (1.00 g, 4 mmol) in glacial acetic acid (10 mL) red fuming nitric acid (1 mL) was added dropwise. The reaction mixture was kept at 0 °C for 10-15 min (TLC monitoring) and then poured into water. The precipitate obtained was filtered off and air-dried. Recrystallization from ethanol with charcoal afforded nitroketone 2 as yellow crystals (0.76 g, 65 %).

Mp: 147-148 °C (ethanol).

IR (KBr): 1695, 1640 cm^-1.

¹H NMR (CDCl₃, 60 MHz, ppm): 2.35 (s, 3H, CH₃), 3.97 (s, 3H, OCH₃), 4.03 (s, 3H, OCH₃), 6.14 (d, 1H, J = 3.2, 3-H_Fur), 6.95 (d, J = 3.2, 4-H_Fur), 6.98 (s, 1H, H_Ar), 7.68 (s, 1H, H_Ar).

Anal. calc. for C₁₄H₁₃NO₆: C 57.73, H 4.50, N 4.81; Found: C 57.79, H 4.42, N 4.77.