Related Products of 17325-26-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
Methyl 1H-imidazole-4-carboxylate (500?mg, 3.96?mmol, 1.0 equiv.) was suspended in dry THF (30?mL). Sodium hydride (60% in mineral oil, 238?mg, 5.95?mmol, 1.5 equiv.) was added at 0?C. After 0.5?h of stirring, Hoffer’s chloro sugar (2.29?g, 5.95?mmol, 1.5 equiv.) was added in three portions over 1?h. The reaction mixture was stirred at ambient temperature overnight, and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (100?mL) and washed with water (3?*?25?mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. After purification by column chromatography (cyclohexane:ethyl acetate 2:1???ethyl acetate), compound 6 was obtained as a white solid (965?mg, 2.02?mmol, 51%). HRMS ESI m/z: [M?+?Na]+ 501.1649 (calcd. 501.1638). Elemental analysis (%): found: C 65.1, H 5.4, N 5.8; calcd. for C26H26N2O7: C 65.3, H 5.5, N 5.9. 1H NMR (400?MHz, CDCl3), delta/ppm: 7.94-7.90 (m, 2H, Tol), 7.89-7.85 (m, 2H, Tol), 7.76 (d, 1.4?Hz, 1H, H5), 7.70 (d, 1.4?Hz, 1H, H2), 7.28-7.21 (m, 4H, Tol), 6.13 (dd, 8.1?Hz, 5.6?Hz, 1H, H1′), 5.65 (dt, 6.1?Hz, 2.4?Hz, 1H, H3′), 4.62 (d, 3.7?Hz, 2H, H5′, H5″), 4.58 (td, 3.7?Hz, 2.4?Hz, 1H, H4′), 3.83 (s, 3H, OCH3), 2.75 (ddd, 14.2?Hz, 5.7?Hz, 2.4?Hz, 1H, H2′), 2.64 (ddd, 14.2?Hz, 8.1?Hz, 6.2?Hz, 1H, H2″), 2.42 (s, 3H, CH3), 2.40 (s, 3H, CH3). 13C NMR (101?MHz, CDCl3), delta/ppm: 166.1 (C=O (Tol)), 165.8 (C=O (Tol)), 162.8 (C=O), 144.6 (Tol), 144.2 (Tol), 136.2 (C2), 134.4 (C4), 129.7 (Tol), 129.6 (Tol), 129.3 (Tol), 129.3 (Tol), 126.5 (Tol), 126.2 (Tol), 122.5 (C5), 86.6 (C1′), 83.1 (C4′), 74.8 (C3′), 63.8 (C5′), 51.6 (OCH3), 39.6 (C2′), 21.7 (CH3), 21.6 (CH3).
The synthetic route of Methyl 1H-imidazole-5-carboxylate has been constantly updated, and we look forward to future research findings.
Reference:
Article; Sandmann, Nikolas; Defayay, Denise; Hepp, Alexander; Mueller, Jens; Journal of Inorganic Biochemistry; vol. 191; (2019); p. 85 – 93;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem