Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2005-10-9, name is 6H-Benzo[c]chromen-6-one, A new synthetic method of this compound is introduced below., Formula: C13H8O2
Magnesium (0.190 g, 7.50 mmol) was placed into an oven-dried round bottom flask and flushed with Ar for 30 min while stirring. 4-Bromobiphenyl 5 (1.75 g, 7.50 mmol), anhydrous THF (10 mL), and a crystal of I2 were then added and the reaction stirred for 1.5 h under Ar. During this time 6H-benzo[c]chromen-6-one 9 (0.981 g, 5.00 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The flask was cooled to 0 C with an ice bath and sparged for 30 min with Ar. The arylmagnesium bromide solution was transferred to the solution containing 9 at 0 Cvia cannula under Ar pressure. The cooling bath was removed, and the reaction was stirred for 18 h. 50 mL of sat. NH4Cl was added to the reaction and subsequently extracted 3x with 25 mL of Et2O. The combined organics were dried with Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in25 mL of diethyl ether and cooled to 0 C in an ice bath and stirred very rapidly. A chilled (0 C) solution of 70% perchloric acid in acetic anhydride (1:3 by volume) was slowly added drop-wise to the stirring ethereal solution until a colored precipitate formed. The crude product was filtered and recrystallized in glacial acetic acid to yield orange-yellow needles (1.36 g, 63%). mp 234e236 C. 1H NMR(400 MHz, CDCl3/CF3CO2D): d 8.93 (d, J 8.3 Hz, 1H), 8.87 (d,J 8.3 Hz, 1H), 8.79 (d, J 8.3 Hz, 1H), 8.61 (t, J 8.3 Hz, 1H), 8.36(d, J 8.5 Hz, 2H), 8.29 (d, J 8.5 Hz, 1H), 8.20-8.04 (m, 5H), 7.80-7.77 (m, 2H), 7.61-7.52 (m, 3H). 13C NMR (100 MHz, CDCl3/CF3CO2D): d 183.8, 151.5, 150.0, 143.9, 139.6, 138.1, 136.2, 134.6,134.2, 132.0, 130.8, 129.8, 129.4, 128.6, 127.9, 127.6, 123.1, 123.9,121.5, 120.6, 119.9. IR (ATR) nmax: 1597, 1542, 1069 cm1. HRMS (ESI)m/z calcd for C25H17O [M] 333.1279, found 333.1276.
The synthetic route of 2005-10-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J.; Tetrahedron; vol. 76; 23; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics