Ethyl Acetate → 2-(N,N-Diethylamino)-4-(hydroxymethyl)thiazole

Participants

Reaction Conditions

Reaction Steps

A solution of 3.14 ml of lithium aluminum hydride in toluene was diluted in a dry flask under N2 atmosphere with 30 ml of THF. The resulting mixture was cooled to 0° C. and treated dropwise with a solution of 1.43 g (6.28 mmol) of ethyl 2-(N,N-diethylamino)thiazole-4-carboxylate in 5 ml of THF. After addition, the solution was allowed to warm slowly to ambient temperature, stirred for 1 h, recooled to 0° C., and treated with a small amount of aqueous Rochelle's salt followed by ethyl acetate. After stirring, the slurry was filtered, washed with additional ethyl acetate, and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography using methanol in chloroform to provide 0.864 g (73%) of the desired compound, Rf 0.17 (4% methanol in chloroform). Mass spectrum: (M+H)+=187.

Provenance & Evidence