preparation | 1-[2-(aminooxy) ethoxy] ethylene was prepared as follows: step A:2-(2-(vinyloxy) ethoxy) isoindoline -1, 3-dione to 2-(vinyloxy) ethanol (20.4mL,227mmol), to a solution of triphenylphosphine (59.5g,227mmol) and N-hydroxyphthalimide (37.0g,227mmol) in THF(450mL) was added DEAD(35.9mL). About 227mmol at 0 °c under N2 atmosphere). After stirring at room temperature for 16 h, the reaction mixture was concentrated in vacuo. The residue was filtered, washed with chloroform, and the filtrate was concentrated in vacuo. The residue was purified by SiO2 column chromatography (Hexane: EtOAc = 2:1) to give 2-(2-(vinyloxy) ethoxy) isoindoline -1, 3-dione (32.5g,61.4%) as a yellow solid. To 2-(2-(vinyloxy) ethoxy) isoindoline -1, 3-dione (32.0g,137mmol) in DCM(96.0mL) to the above solution was added dropwise an aqueous solution of methylhydrazine (15.8mL,137mmol). Room temperature. After stirring for 1 hour at room temperature, The resulting suspension was diluted with diethyl ether and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hexane: EtOAc = 3:2 to 1:1) to give O-(2-(vinyloxy) as a yellow oil ethyl)-hydroxylamine (10.7g,76%). |