Nitromethane → Tetrahydro-3-(2-nitroethenyl)furan
Reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6]CN)=[CH:2]1.[N+:9]([CH3:12])([O-:11])=[O:10]>>[N+:9]([CH:12]=[CH:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)([O-:11])=[O:10]Participants
3
Procedure
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]+.
Sources & evidence
- ORD record
- ord-dfec4338cc28430ab5a1abb892a67069
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037916B2
Reaction notes
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