2-Chloroethanol → HCID 178478509, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxybenzimidazole (3.1 g, 32.4 mmol), triphenylphosphine (12.75 g, 48.6 mmol) and 2-chloroethanol (5.2 g, 64.8 mmol) in tetrahydrofuran (75 mL) at 0-5° C. was added over 30 min a solution of diethyl azodicarboxylate (8.5 g, 48.7 mmol) in tetrahydrofuran (75 mL). The mixture was warmed to 23° C. and stirred for 48 hr. The solvent was removed under vacuum to give a dark brown oil. Purification by chromatography (silica gel, ethyl acetate-1% 2M NH3 in methanol) afforded 2.9 g (63.8%) of a solid residue that was crystallized from ethyl acetate to give the title compound as a white solid, mp 153-154° C.

Provenance & Evidence