Synthetic Route of 5428-09-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 5428-09-1 as follows.
Example 7-2 Preparation of 2-(4-(trimethylsilyl)but-2-en-1-yl)isoindoline-1,3-dione 12 To a solution of 2-allylisoindoline-1,3-dione 11 (13.0 g, 69.4 mmol) in CH2Cl2 (500 mL) was added AllylTMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 °C 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. NaCl solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 (3 * 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. Column chromatography over SiO2 (Cyclohexane/ EtOAc = 85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 percent) as a yellow resin. Rf: 0.57 (Cyclohexane/EtOAc = 85:15) 1H NMR (300 MHz, CDCl3) delta = -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). 13C NMR (75 MHz, cdcl3) delta = -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.
According to the analysis of related databases, 5428-09-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem