Synthesis
1-[2-(Aminooxy)ethoxy]ethylene is prepared as follows:
Step A: 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione
To a solution of 2-(vinyloxy)ethanol (20.4 mL, 227 mmol), triphenylphosphine (59.5 g, 227 mmol), and N-hydroxyphthalimide (37.0 g, 227 mmol) in THF (450 mL) was added DEAD (35.9 mL) N2 atmosphere at 0 C for ~227 mmol). After stirring for 16 hours at room temperature, the reaction mixture was concentrated in vacuum. The residue was filtered, washed with chloroform and the filtrate was concentrated in vacuum. The residue was purified by SiO2 column chromatography (hexane:EtOAc = 2:1) to give 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.5 g, 61.4%) as a yellow solid.
Aqueous solution of methylhydrazine (15.8 mL, 137 mmol) was added dropwise to a solution of 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.0 g, 137 mmol) in DCM (96.0 mL). Room temperature. After stirring for 1 hour at room temperature, the resulting suspension was diluted with ether and filtered. The filtrate was concentrated in vacuum. The residue was purified by column chromatography on SiO2 (hexane:EtOAc = 3:2 to 1:1) to give O-(2-(vinyloxy)ethyl)-hydroxylamine (10.7 g, 76%) as a yellow oil.
