O-(2-(vinyloxy)ethyl)hydroxylamine synthesis
- Product Name:O-(2-(vinyloxy)ethyl)hydroxylamine
- CAS Number:391212-29-6
- Molecular formula:C4H9NO2
- Molecular Weight:103.12
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
391212-30-9
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391212-29-6
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Yield:391212-29-6 76%
Reaction Conditions:
with methylhydrazine in dichloromethane;water at 20; for 1 h;
Steps:
2.B
Step B: O-(2-(vinyloxy)ethyl)hydroxylamine To a solution of 2-(2-(vinyloxy)ethoxy)isoindoline-1,3-dione (32.0 g, 137 mmol) in DCM (96.0 mL) was added dropwise an aqueous solution of methylhydrazine (15.8 mL, 137 mmol) at room temperature. After being stirred for 1 h at room temperature, the resultant suspension was diluted with diethyl ether and filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:2 to 1:1) to give O-(2-(vinyloxy)ethyl)-hydroxylamine (10.7 g, 76%) as a yellow oil. 1H NMR (CDCl3, Varian 400 MHz) δ 3.85-3.93 (4H, m), 4.03 (1H, dd, J=6.8, 2.0 Hz), 4.22 (1H, dd, J=14.2, 2.0 Hz), 5.51 (2H, brs), 6.50 (1H, dd, J=14.2, 6.8 Hz).
References:
CHEMIZON, A DIVISION OF OPTOMAGIC CO., LTD. US2012/238599, 2012, A1 Location in patent:Page/Page column 19