3-Chloro-1-butene → 2-(But-3-en-2-yl)isoindoline-1,3-dione

HRID 243211

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].C(=O)([O-])[O-].[K+].[K+].Cl[CH:20]([CH3:23])[CH:21]=[CH2:22]>CN(C=O)C>[CH3:22][CH:21]([N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[CH:20]=[CH2:23]

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

To a suspension of potassium phthalimide (7.08 g, 38.2 mmol) in DMF (60 mL) was added potassium carbonate (1.06 g, 7.6 mmol) and 3-chloro-1-butene (5.0 mL, 49.7 mmol). The mixture was heated under reflux in a bath at 135° C. for 4 h. The cooled reaction mixture was concentrated in vacuo and water (65 mL) was added over 5 minutes with rapid stirring at 40° C. The resulting suspension was cooled in an ice bath and then the solid was collected by filtration, washed with water (2×7 mL), then ethanol/water (45:55, 14 mL) and dried in vacuo at 50° C. for 16 h to give the title compound as a buff solid (5.0 g, 65%). 1H NMR ((CD3)2SO, 300 MHz): 7.87-7.83 (4H, m), 6.12 (1H, ddd, J=17.3, 10.5, 5.7 Hz), 5.17 (1H, dt, J=17.3, 1.4 Hz), 5.13 (1H, dt, J=10.4, 1.4 Hz), 4.88-4.78 (1H, m), 1.51 (3H, d, J=7.1 Hz)

Aufarbeitung

temperatureThe mixture was heated
customThe cooled reaction mixture
concentrationwas concentrated in vacuo and water (65 mL)
additionwas added over 5 minutes
temperatureThe resulting suspension was cooled in an ice bath
filtrationthe solid was collected by filtration
washwashed with water (2×7 mL)
dry with materialethanol/water (45:55, 14 mL) and dried in vacuo at 50° C. for 16 h

Quellen und Nachweise

ORD-Eintrag: ord-f0e566c1663c4c8091a2f424baf24c40
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653089B2

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