Dimethylformamide → 2-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Participants

Reaction Steps

A solution of 2-fluoro-1-triphenylmethylimidazole (3.28 g.) in dry THF (33 ml.) was treated, under argon, at -75° with two equivalents of t-butyl lithium (10 ml. of a 1.93M solution in pentane). After stirring 3 hours at -75°, DMF (1.5 ml.) was added. The reaction mixture was kept a further hour at -75° then allowed to warm up slowly to room temperature. The reaction was worked up by diluting with ether, washing with 2N HCl followed by brine. The ether layer was concentrated under a steam of argon to give 4-formyl-2-fluoro-1-triphenylmethylimidazole, (2.2 g.) m.p. 177°-179°.

Provenance & Evidence