4-Hydroxymethylthiazole

Chemical Properties

Uses

Synthesis

14527-43-6

7036-04-6

The general procedure for the synthesis of 4-hydroxymethylthiazole from ethyl 4-thiazolecarboxylate was as follows: - Lithium aluminum hydride (1M tetrahydrofuran solution, 1.5 mL) was slowly added dropwise to a stirred tetrahydrofuran solution (4 mL) of ethyl 4-thiazolecarboxylate (224 mg) at 0 °C. - The reaction mixture was naturally warmed to room temperature with stirring for 1 hour. - Ethyl acetate (20 mL), water (1 mL), 2M sodium hydroxide solution (2 mL), and water (3 mL) were added sequentially to the reaction mixture. - The precipitate formed was removed by filtration through diatomaceous earth (iT). - The filtrate was concentrated to give 4-hydroxymethylthiazole (150 mg, 92% yield). - Nuclear magnetic resonance hydrogen spectroscopy (DMSO-d6) data: δ 4.12 (s, 2H), 7.47 (s, 1H), 9.03 (s, 1H).

References