Hydrochloric Acid → methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

43 ml (43 mmol) of a 1 molar solution of diisobutyl-aluminium hydride in tetrahydrofuran within 20 minutes were added dropwise to a solution of 13.5 g (42.84 mmol) of dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazol-4,5-dicarboxylate in 220 ml of tetrahydrofuran under an argon atmosphere at −70° C. The mixture was stirred for a further 4 hours at −70° C., then 20 ml of a mixture of 1M hydrochloric acid and tetrahydrofuran were added dropwise. After heating to ambient temperature approx. 200 ml of water were added and the mixture was extracted three times with 70 ml of ethyl acetate. The extracts were dried and evaporated down, and the crude product thus obtained was purified by column chromatography (silica gel; eluant:petroleum ether with 20–50% ethyl acetate).

Provenance & Evidence