Water → 5H,6H,7H,8H-imidazo(1,5-a)pyridin-8-one

Participants

Reaction Steps

4-Hydroxy-1-(1-trityl-1H-imidazol-4-yl)butan-1-one (25.22 g) was dissolved in tetrahydrofuran (120 ml). Triethylamine (0.021 ml) and methanesulfonyl chloride (0.012 ml) were added and the mixture was stirred at room temperature for 1 h. Water (100 ml) was added under ice-cooling and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Acetonitrile (100 ml) was added and the mixture was refluxed under heating for 2 h. The reaction mixture was concentrated to dryness and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol=20:1→5:1) and washed with diethyl ether to give the title compound (2.10 g) as a pale-brown powder.

Provenance & Evidence