4-Lithio-1-tritylimidazole as a synthetic intermediate. Synthesis of imidazole-4-carboxaldehyde

Reaction of 4-iodo-1-tritylimidazole with n-butyllithium at –79°, followed by rapid quenching of the reaction mixture with DMF, gives good yields of 1-tritylimidazole-4(5)-carboxaldehyde, the isolation of which demonstrates the intermediacy of 4-lithio-1-tritylimidazole. This species should be destabilized by repulsive interaction of the negative charge on C-4 with the adjacent lone pair electrons on N-3 (the ALP effect). The isolation of 1-tritylimidazole-4(5)-carboxaldehyde in good yield and the versatility of the aldehyde functionality make 4-lithio-1-tritylimidazole a useful synthetic intermediate.

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