Electric Literature of 33016-47-6, These common heterocyclic compound, 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde, its 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.
To a solution of (4a/1?, 10bS)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10-phenanthroline (0.25 g, 1.3 mmol), 1-(triphenylmethyl)-1 /-/-imidazole-4-carbaldehyde (similar methods as described in J. Org. Chem. 2002, 67, 620-624; 0.89 g, 2.6 mmol) , and acetic acid (0.078 g, 1.3 mmol) in 5 ml_ of 1 ,2-dichloroethane was added sodium triacetoxyborohydride (0.82 g, 3.9 mmol). The mixture was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted 3 times with 10 mL of dichloromethane. The organic phase was concentrated and the residue purified by silica chromatography eluting with a 0% to 5% gradient of 2 M ammonia in methanol with dichlromethane as co-eluent to yield 0.27 g (41%) of (4afl,1 ObS)-I -{[1-(triphenylmethyl)-1 H-imidazol-4-yl]methyl}-1 ,2,3,4,4a,5,6,1 Ob- octahydro-1 ,10-phenanthroline. 1 H NMR (400 MHz, METHANOL-D4) delta ppm 1.6 (m, 5 H), 2.0 (m, 1 H), 2.3 (m, 2 H), 2.7 (m, 1 H), 2.9 (m, 1 H), 3.0 (m, 1 H), 3.4 (m, 2 H), 3.8 (m, 1 H), 6.8 (s, 1 H), 7.1 (m, 6 H), 7.2 (dd, J=U, 4.6 Hz, 1 H), 7.3 (s, 1 H), 7.3 (m, 9 H), 7.5 (d, J=8.1 Hz, 1 H), 8.2 (d, J=4.4 Hz, 1 H); MS m/z 511 (M+1).
The synthetic route of 33016-47-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem