Imidazole → 2-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride

Participants

Reaction Conditions

Reaction Steps

[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.

Provenance & Evidence