Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate → (2-Bromo-4-methylthiazol-5-yl)methanol

Participants

Reaction Steps

To a solution of ethyl 2-bromo-4-methylthiazole-5-carboxylate (7 g, 28 mmol) in EtOH (120 mL) and H2O (20 mL) was added portion-wise NaBH4 (3.2 g, 84 mmol). After the addition, the mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc=5:1) showed the reaction was complete. The reaction mixture was carefully concentrated in vacuum. The residue was separated between EtOAc (50 mL) and H2O (50 mL). The inorganic layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuum to give the title compound as a colorless oil (3.8 g, 65%).

Provenance & Evidence