Electric Literature of 4224-69-5, 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 4224-69-5 as follows.
To a dry nitrogen-flushed 15 mL round bottom flask was added dry THF (5.9 mL) and iPr2NH(0.87 mL, 6.21 mmol, 1.05eq.). The flask was cooled to -78 C andn-BuLi(2.48 mL, 6.21 mmol, 1.05eq.) was added slowly. The mixture wasstirred at 0 C for 10 minutes and then cooled back down to -78 C and cannulated into a -78 C solution of starting material(1.16 g, 5.91 mmol, 1.00eq.) in THF (5.9 mL).The reaction mixture was stirred for 30 min at -78 C and then methyl(2-bromomethyl)acrylate wasadded (0.87 mL, 7.09 mmol,1.20 eq.) via syringe. The reaction wasstirred for 1h at -78 C then 3 h at r.t. The reaction was quenched with H2O(10 mL) and extracted with Et2O (2 x 20 mL). The combinedorganics were washed with brine (10 mL), dried withMgSO4, rotovapped, and chromatographedto yield the desired product was a white solid (1.5338 g, 5.21 mmol) in 88% yield. 1H NMR (300 MHz, CDCl3)delta 8.03 – 7.91 (m, 2H), 7.47-7.38 (m, 1H), 7.36 – 7.13 (m, 7H), 6.07 (s,1H), 5.41 (s, 1H), 4.95 (t, J = 7.2Hz, 1H), 3.71 (s, 3H), 3.23 (dd, J = 14.1, 7.3 Hz, 1H), 2.79 (dd, J = 14.0, 7.2 Hz, 1H).. 13C NMR (75 MHz, CDCl3) delta 198.7, 167.2, 138.7,137.3, 136.5, 132.8, 128.8, 128.6, 128.4, 128.2, 128.0, 127.9, 127.1, 52.2,51.8, 36.7.
According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.
Reference:
Article; Ramachandran, P. Veeraraghavan; Helppi, Matthew A.; Lehmkuhler, Arlie L.; Marchi, Jennifer M.; Schmidt, C. Max; Yip-Schneider, Michele T.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 19; (2015); p. 4270 – 4273;,
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