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

関与物質

反応手順

A solution of ethyl 2-bromoimidazo[5,1-b] thiazole-7-carboxylate (84 mg, 0.31 mmol) in tetrahydrofuran (7 ml) was cooled to −50° C. A toluene solution of diisobutylaluminium hydride (1.01 M solution; 1.06 ml, 1.07 mmol) was added dropwise to the cooled 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 1.5 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. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1→30:1) to give 2-bromo-7-hydroxymethylimidazo[5,1-b]thiazole (44 mg, 61%) as a white solid and 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (19 mg, 26%) as a white solid.

情報源と証拠