Diisopropylamine → 1-Ethenyl-1H-imidazole-2-carboxaldehyde

Participants

Reaction Steps

To a cold (-78° C.) solution of 6.55 ml (0.047 mole) of diisopropylamine in 125 ml of tetrahydrofuran was added 16.99 ml (, 042 mole) of a 2.5M solution of n-butyl lithium over a period of 15 minutes and the resulting reaction allowed to stir for 30 minutes. 1-Vinylimidazole (3.85 ml 0.042 mole) was added over a 10 minute period and the mixture stirred for one hour. Ethyl formate (3.43 ml, 0.042 mole) was then added over 5 minutes and the mixture stirred for one hour and was then poured into a saturated ammonium chloride solution. The product was extracted with ethyl acetate, and the extracts combined, dried over magnesium sulfate and concentrated to an orange oil. The residue was chromatographed on 200 g of silica gel using 10% ethyl acetate in chloroform to give 2.23 g of the product as a crystalline material.

Provenance & Evidence