Dimethylformamide → HCID 22064722, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred, cooled (−75° C.) light orange solution of 3.79 g 1-(2-benzyloxy-ethyl)-1H-benzoimidazole in 80 ml THF under argon atmosphere was added dropwise 9.4 ml n-butyllithium solution (1.6 M in hexanes) for 15 min (temperature of the solution below −71° C. during the addition; reaction mixture turning to orange). When addition was complete, stirring at −75° C. was continued for 1 h 30. The reaction mixture was then treated with 1.44 ml DMF within 5 min and stirring at −75° C. was continued for 4 h. Then 40 ml of saturated NH4Cl-solution was added to the reaction mixture which was subseqently allowed to warm to r.t. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified by chromatography on silica gel using a gradient from cyclohexane to cyclohexane/EtOAc 65:35 to give 1.09 g 1-(2-benzyloxy-ethyl)-1H-benzoimidazole-2-carbaldehyde as viscous yellow oil. MS 281.0 ([M+H]+)

Provenance & Evidence