Sodium hydride → HCID 86257583, compound

Participants

Reaction Steps

To a suspension of NaH 60% (37.65 g, 0.94 mol) in DMF (175 ml) was carefully added a solution of 1-H-imidazole-4-carboxaldehyde (75.36 g, 0.784 mol) in DMF (350 ml). The mixture was stirred at room temperature for 0.5 h, then a solution of 4-bromomethylbenzoic acid methyl ester (215.6 g, 0.94 mol) in DMF (475 ml) was added and the reaction was stirred overnight. The solvent was evaporated under vacuum, the residue taken in ethyl acetate and water. The organic phase was separated, washed with brine and dried over MgSO4. The crude oil was purified several times by flash chromatography on silica gel using (toluene/ethyl acetate/NH4OH: 60/40/1) as eluent to give quantitatively the desired products.

Provenance & Evidence