Toluene → 2-Bromo-7-hydroxymethylimidazo[5,1-b]thiazole

Participants

Reaction Steps

A solution of ethyl 2-bromoimidazo[5,1-b] thiazole-7-carboxylate (160 mg, 0.58 mmol) in dichloromethane (6 ml) was cooled to −78° C. A toluene solution of diisobutylaluminium hydride (1.01 M solution; 1.7 ml, 1.75 mmol) was added dropwise to the solution, and the mixture was stirred at the same temperature for 15 min. After the completion of the reaction, a saturated aqueous potassium sodium tartrate solution was added thereto, and the mixture was stirred at room temperature for one hr and was extracted with ethyl acetate (7 ml×3). The organic layer was washed with saturated brine and was then dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure to give 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (128 mg, 94%) as a white solid.

Provenance & Evidence