Electric Literature of 33016-47-6,Some common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, molecular formula is C23H18N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture comprising compound 158B (350 mg; 0.88 mmol) and 1-trityl-1H-imidazole-4-carboxaldehyde (352 mg; 1.00 mmol) dissolved in 1,2-dichloroethane (DCE) (4.5 ml) in the presence of acetic acid (0.3 ml) is stirred for 5 minutes at room temperature and sodium triacetoxyborohydride (233 mg; 1.10 mmol) is then added. The mixture is stirred overnight at room temperature and is then diluted with ethyl acetate and washed successively with saturated NaHCO3 solution, with water, and with saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated. This crude reaction, product is then purified by flash chromatography (gradient: 4/1 and then 2/1 CH2Cl2/acetone) to give the desired product (304 mg; 48%). [0268] 1H NMR, DMSO-d6 (ppm): 1.88 (m, 2H); 2.00 (s, 3H); 2.33 (m, 2H); 3.63 (s, 3H); 4.03 (d, 2H, 5.2 Hz); 4.50 (m, 1H); 5.45 (t, 1H, 5.6 Hz); 6.55 (s, 1H); 6.70 (s, 1H); 6.76 (d, 1H, 8.7 Hz); 7.01 (m, 6H); 7.21 (d, 1H, 8.7 Hz); 7.25 (s, 1H); 7.31-7.41 (m, 13H); 7.55 (d, 1H, 7.4 Hz); 7.73 (d, 3H, 9.4 Hz); 11.35 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Trityl-1H-imidazole-4-carbaldehyde, its application will become more common.
Reference:
Patent; Perez, Michel; Lamothe, Marie; Hill, Bridget; Etievant, Chantal; US2004/204417; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem