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

2-Furaldehyde (18.2 g, 190 mmol) and ammonium acetate (13 g, 169 mmol) were added to nitromethane (169 mL) and the mixture was heated to reflux for 45 min. The solution was concentrated and dichloromethane (250 mL) was added. The dichloromethane solution was washed with water (2×250 mL), dried over sodium sulfate, and filtered to obtain the crude product. Purification by column chromatography (silica gel, ethyl acetate/heptane=1/10 to 2/3) afforded pure 2-(2-nitrovinyl)-furan (14 g, 53.0%) as a yellow powder (M.P. 71-74° C.). 1H NMR (Field: 300 MHz, Solvent: CDCl3/TMS) δ (ppm): 7.78 (d, 1H, J=13.2 Hz), 7.59 (m, 1H), 7.52 (d, 1H, J=13.5 Hz), 6.90 (d, 1H, J=3.6 Hz), 6.58 (m, 1H). 13C NMR (Field: 75 MHz, Solvent: CDCl3/TMS) δ (ppm): 146.90, 146.67, 134.93, 125.51, 120.12, 113.46.

1. temperaturethe mixture was heated
2. temperatureto reflux for 45 min
3. concentrationThe solution was concentrated
4. additiondichloromethane (250 mL) was added
5. washThe dichloromethane solution was washed with water (2×250 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customto obtain the crude product
9. customPurification by column chromatography (silica gel, ethyl acetate/heptane=1/10 to 2/3)

ORD record

ord-c5d479abcd9e488b8f7ea141be34bc51

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349833B2