Continuously updated synthesis method about 2-Allylisoindoline-1,3-dione

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Allylisoindoline-1,3-dione, and friends who are interested can also refer to it.

Adding a certain compound to certain chemical reactions, such as: 5428-09-1, name is 2-Allylisoindoline-1,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 5428-09-1, SDS of cas: 5428-09-1

To a solution of 2-allylisoindoline-1,3-dione 11(13.0 g, 69.4 mmol) in CH2CI2 (500 mL) was added AIIyITMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 ¡ãC and stirred under reflux for 4 h.Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCI solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (3 x 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removedunder reduced pressure. Column chromatography over SiC2 (Cyclohexane/ EtOAc =85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 percent) as a yellow resin.R: 0.57 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = -0.10?0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72(d, J= 8.8 Hz, 0.4 H), 4.21 (d, J= 6.5 Hz, 1.6 H), 4.29 (dd, J= 14.5, 5.9 Hz, 0.4 H),5.26 ? 5.47 (m, 0.8 H), 5.56 ? 5.70 (m, 0.2 H), 5.70 ? 5.87 (m, 0.8 H), 5.94 ? 6.09 (m,0.2 H), 7.65 ? 7.74 (m, 2H), 7.79 ? 7.88 (m, 2H).?3C NMR (75 MHz, cdcl3) 6 = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51,121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Allylisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem