Reacción #1049534

Ecuación de reacción

potassium phthalimide

2-chloroethyl vinyl ether

dimethylformamide

→

2-vinyloxyethyl phthalimide

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Otroprecipitates the crude product
3. 3
   FiltraciónFiltration and recrystallization from 3×500 ml methanol and 2×500 ml ethyl acetate with charcoal treatment
4. 4
   Secadodrying in the last step with magnesium sulphate
5. 5
   Otrogave 55 g (47% based on potassium phthalimide) of the pure 2-vinyloxyethyl phthalimide as slightly yellowish needles

Procedimiento

A 1000 ml three-necked flask was charged with potassium phthalimide (100 g, 540 mmol), 2-chloroethyl vinyl ether (100 g, 940 mmol), tetra-n-butylammonium bromide (2 g) and 250 ml dimethylformamide. The reaction mixture was refluxed at 100° C. overnight (approximately 12 hours), with magnetic stirring and under argon atmosphere. After cooling to room temperature, the reaction mixture was poured into 1000 ml of distilled water which precipitates the crude product. Filtration and recrystallization from 3×500 ml methanol and 2×500 ml ethyl acetate with charcoal treatment and drying in the last step with magnesium sulphate gave 55 g (47% based on potassium phthalimide) of the pure 2-vinyloxyethyl phthalimide as slightly yellowish needles. The product was confirmed by 1H NMR (CDCl3) δ (ppm)=3.95 (s,2H+2H+1H), 4.20(d,1H), 6.40(m,1H), 7.70(m,2H), 7.85(m,2H).

Fuente