反应详情

温度

0 °C

[1-(Tetrahydro-furan-2-yl)-1H-imidazol-2-yl]-methanol was prepared from imidazole and dihydrofuran according to a procedure in the literature (Song et al. J. Org Chem. 1999, 64, 1859-1867). To a solution of [1-(tetrahydro-furan-2-yl)-1H-imidazol-2-yl]-methanol (7.0 g, 41.7 mmol) in dry CH2Cl2 (80 mL) at 0° C. under N2 was added dropwise SOCl2. The resulting solution was stirred at 0° C. for 3 h and allowed to warm up gradually to ambient temperature overnight. The mixture was cooled in a dry ice-ethylene glycol bath before saturated NaHCO3 (200 mL) was added carefully. The resulting mixture was extracted with CH2Cl2 (3×100 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo. The crude 2-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride (5.7 g, 74%) was obtained as a brown oil; ESI MS m/z 187 [C8H11ClN2O+H]+. The product was used immediately in the next reaction.

1. temperatureto warm up gradually to ambient temperature overnight
2. additionwas added carefully
3. extractionThe resulting mixture was extracted with CH2Cl2 (3×100 mL)
4. dry with materialThe combined extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo