Nitromethane → Tetrahydro-3-(2-nitroethenyl)furan

Participants

Reaction Steps

Dichloromethane extraction of tetrahydrofuran-3-carboxaldehyde in water (50%, 2 mL) gave pure aldehyde (0.72 g, 7.2 mM) that was reacted with nitromethane in an analogous manner as used for the preparation of 2-Furan-3-yl-ethylamine above, to yield 3-(2-Nitrovinyl)-tetrahydrofuran (0.57 g, 55% yield) after column chromatography (elution with 30% ethyl acetate/Hexanes). The vinyl-nitro compound was reduced with LAH as described for the synthesis of 2-(furan-2-yl-)ethylamine, except that 1 M HCl/Et2O (5 mL) was added to the filtered solvent prior to evaporation to yield 2-(Tetrahydrofuran-3-yl) ethylamine as the HCl salt (30% yield). ESI-MS (m/z) 116 [M+H]+.

Provenance & Evidence