Dimethylformamide → 2-Vinyloxyethyl phthalimide

HRID 962352

Reaktionsgleichung

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH:13]([O:15][CH2:16][CH2:17]Cl)=[CH2:14].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:13]([O:15][CH2:16][CH2:17][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])=[CH2:14]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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).

Aufarbeitung

temperatureAfter cooling to room temperature
customprecipitates the crude product
filtrationFiltration and recrystallization from 3×500 ml methanol and 2×500 ml ethyl acetate with charcoal treatment
dry with materialdrying in the last step with magnesium sulphate
customgave 55 g (47% based on potassium phthalimide) of the pure 2-vinyloxyethyl phthalimide as slightly yellowish needles

Quellen und Nachweise

ORD-Eintrag: ord-4831ff2a59064217aa60d2227bafbb56
Quelldatensatz: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05759404

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