Adding a certain compound to certain chemical reactions, such as: 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, belongs to imidazoles-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 870837-18-6, name: 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde
Under ice-cooling, L-selectride (3.73 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (25 mL) solution containing (4R,6S)-6-(4-chlorophenyl)-1,1-dimethyltetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (850 mg). Stirring was continued for 1 hour at the same temperature. A 5 N sodium hydroxide solution (566 muL) was added to the reaction solution, and stirring was continued for 20 minutes at 0 C. Next, hydrogen peroxide solution (275 muL, 35% solution) was added, and stirring was continued for 20 minutes at 0 C. Sodium bisulfite (294 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (25 mL) and triphenyl phosphonium bromide (990 mg) was added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl) benzaldehyde (674 mg) and triethylamine (781 muL) were added, and stirring was continued for 10 hours at room temperature. Ethyl acetate and brine were added, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and ethyl acetate (1 mL) was added to the residue, and diethyl ether (15 mL) was added gradually, and the precipitated solid was collected by filtration, and the title compound (790 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 478 [M++H]. 1H-NMR (CDCl3) delta(ppm): 1.45 (s, 3H), 1.58 (s, 3H), 1.81-1.92 (m, 1H), 2.02-2.14 (m, 2H), 2.29 (s, 3H), 2.34-2.45 (m, 1H), 3.85 (s, 3H), 3.94 (dd, J=11.6, 5.2 Hz, 1H), 5.14 (d, J=9.2 Hz, 1H), 6.78 (s, 1H), 6.91 (s, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.24-7.32 (m, 5H), 0.53 (d, J=9.6 Hz, 1H), 7.69 (d, J=1.6 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, and friends who are interested can also refer to it.
Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem