Reference of 1615-14-1,Some common heterocyclic compound, 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, molecular formula is C5H8N2O, 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 suspension of sodium hydride (2mmol, 2eq) in THF (5mL) was treated with a solution of 2-(1H-imidazol-1-yl)ethanol (1mmol, 1eq) in THF (3mL) at 0C. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1h. The mixture was cooled to 0C before addition of 2,4-dichlorobenzyl bromide (1, 1.5mmol, 1.5eq). The resulting mixture was stirred under reflux for 3h. The reaction was quenched by addition of a saturated aqueous solution of NH4Cl (5mL). The aqueous phase was extracted with ethyl acetate (15mL, three times), the organic phase was washed with water (10mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography (SiO2, MeOH/ethyl acetate) afforded 2 as an oil in 65% yield. IR (film): numax: 3109, 2868, 1898, 1589, 1505, 1469, 1075, 813, 737cm-1. 1H NMR (400MHz, CDCl3): delta 7.55 (bs, 1H), 7.37 (s, 1H), 7.24-7.23 (m, 2H), 7.07 (bs, 1H), 6.98 (s, 1H), 4.56 (s, 2H), 4.17 (t, 2H, J=5.1Hz), 3.79 (t, 2H, J=5.1Hz) ppm. 13C NMR (100MHz, CDCl3): delta 137.5, 133.9, 133.88, 133.3, 129.6, 129.4, 129.1, 127.0, 119.4, 70.0, 69.6, 47.0ppm. ESI-TOF-HRMS: m/z calcd for (M+H) C12H12N2Cl2O 271.0405 found 271.0416.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1H-Imidazol-1-yl)ethanol, its application will become more common.
Reference:
Article; Roehrig, Ute F.; Majjigapu, Somi Reddy; Chambon, Marc; Bron, Sylvian; Pilotte, Luc; Colau, Didier; Van Den Eynde, Benoit J.; Turcatti, Gerardo; Vogel, Pierre; Zoete, Vincent; Michielin, Olivier; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 284 – 301;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem