ChemicalBook CAS DataBase List 2-(but-3-en-2-yl)isoindoline-1,3-dione

2-(but-3-en-2-yl)isoindoline-1,3-dione synthesis

6synthesis methods

Product Name:2-(but-3-en-2-yl)isoindoline-1,3-dione
CAS Number:7065-05-6
Molecular formula:C12H11NO2
Molecular Weight:201.22

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Yield:7065-05-6 96%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 140; for 7 h;

Steps:

1 Step 1 : 2-(but-3-en-2-yl)isoindoline-l,3-dione

A mixture of phthalimide potassium (39.3 g, 212 mmol), K₂C0₃ (5.9 g, 42.5 mmol), and DMF (354 ml) was set stirring at RT before adding 3-chloro-l-butene (25.00 ml, 276 mmol). The suspension was fitted with a reflux condenser and heated to 140 °C for 7 h before cooling to RT and pouring in 1.5 L water at 0 °C with rapid stirring. The resulting white precipitate was collected by filtration and was rinsed with cold water. After drying under air for 1 h, the material was transferred to a bottle and dried under vacuum at 50 °C overnight to give 2-(but-3-en-2-yl)isoindoline-l,3-dione (41.05 g, 204 mmol, 96% yield): ^{FontWeight="Bold" FontSize="10"}H NMR (400 MHz, DMSO-d₆) δ ppm 7.75 - 7.94 (4 H, m), 6.11 (1 H, ddd, J=17.3, 10.4, 5.8 Hz), 5.05 - 5.25 (2 H, m), 4.72 - 4.89 (1 H, m), 1.50 (3 H, d, J=7.0 Hz), m/z (ESI, +ve) 202.1 (M+H)⁺.

References:

WO2014/22752,2014,A1 Location in patent:Page/Page column 77