Hydrochloric Acid → Furan, 2-[(1E)-2-nitroethenyl]-

Participants

Reaction Conditions

Reaction Steps

In a 1L 3-necked flask equipped with a mechanical stirrer, thermometer and a dropping funnel was placed 2-furaldehyde 32I (48 g, 0.5 mol) and nitromethane (30.5 g, 0.5 mol) in methanol (100 mL). The resulting mixture was cooled to −5° C. A solution of sodium hydroxide (21 g, 0.525 mol) in water (75 mL) was added at such a rate to maintain internal temperature at 0° C. (45 min). The resulting paste was stirred at 0° C. for 1 hr and then ice cold water (100 mL) was added to get a homogeneous mixture. This mixture was poured into a stirring cold solution of hydrochloric acid (100 mL of concentrate hydrochloric acid in 150 mL of water)over 20 min. After 30 min, yellow solid was collected, washed with water (250 mL) and treated with 2 g of charcoal (Norit A) in boiling ethanol (75 mL). Hot filtered through a pad of celite (7 g) in a steam jacketed Buchner funnel. The pad was washed with hot ethanol (15 mL). The filtrate was placed in a fridge for 1 hr and then yellow solid was collected and air dried to give 44 g (63% yield) of 33I. Hplc analysis showed a purity of 98%. NMR (CDCl3) δ 7.8(q, 2H), 7.8(S br, 1H), 7.1(d, 1H), 6.7–6.9(m, 1H).

Provenance & Evidence