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

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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)

Herkunft & Nachweise