69778-83-2 4-Methoxy-1H-pyrrol-2(5H)-one 574769, apyrrolines compound, is more and more widely used in various.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.69778-83-2,4-Methoxy-1H-pyrrol-2(5H)-one,as a common compound, the synthetic route is as follows.
To a mixture of diethylformamide (3 eq, 5.8 mL) and chloroform (5 mL) at 00C was added dropwise a solution of phosphorus oxybromide (2.5 eq, 12.6 g) in chloroform (15 mL). The resulting suspension was stirred at 0 0C for 30 min, and the sol “vent was removed by rotary evaporation to obtain the Vilsmeier complex as a white solid. After drying in vacuo104USlDOCS 5506941vl EPO for 20 min, the solid was treated with chloroform (10 mL) and cooled to 0 0C. A solution of 4-methoxy-3-pyrrolin-2-one (A, 2 g, 17.7 mmol) in chloroform (20 mL) was added dropwise and the mixture was warmed to room temperature, then heated at 60 0C for 5h. The mixture was poured onto ice (75 mL), and the pH of the aqueous solution was adjusted to pH 7-8 by treatment with NaOH 2N. EtOAc (40 mL) was added to the resulting precipitate and the mixture was filtered over Celite.(R). to remove the black solid containing phosphorus salts.The two layers were separated and the aqueous layer was extracted with EtOAc (3 x 100 mL). The organic layers were combined, washed with brine (3 x 200 mL), dried over Na2SO4, filtered and the solvent was removed by rotary evaporation to furnish the crude enamine intermediate B’.The residue was filtered over a pad of silica gel (50 mL) using a 10percent EtOAC/Hexianes as eluent to obtain the enamine as an oil, which upon drying in vacuo lead to a beige solid.Yield: 3.20 g, 70percent. M/Z: 260.1 [M+l]RMNT 1H (300 MHz, CDCl3): delta (ppm) 1.24-1.37 (m, 6H); 3.31-3.46 (q, 2H); 3.76 (s, 3H), 4.03-4.18 (q, 2H); 5.58 (s, 3H); 6.98 (s, 3H).
69778-83-2 4-Methoxy-1H-pyrrol-2(5H)-one 574769, apyrrolines compound, is more and more widely used in various.
Reference£º
Patent; GEMIN X BIOTECHNOLOGIES INC.; WO2006/89397; (2006); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem