5-Benzothiazolemethanol(9CI)

Synthesis

478169-65-2

394223-37-1

General procedure for the synthesis of benzothiazol-5-ylmethanol from methyl benzo[d]thiazole-5-carboxylate: diisobutylaluminum hydride (DIBAL-H, 50 mL, 1 M hexane solution) was added slowly and dropwise to an anhydrous tetrahydrofuran (50 mL) solution of methyl benzo[d]thiazole-5-carboxylate (5.0 g, 26 mmol) at -78 °C. The reaction mixture was stirred continuously at -78°C for 2 hours. Upon completion of the reaction, the reaction was quenched by the slow addition of water (50 mL) at 0 °C, followed by filtration. The filtrate was extracted with dichloromethane (3 x 100 mL). After combining the organic layers, benzothiazol-5-ylmethanol (2.8 g, 65% yield) was obtained by vacuum concentration, the product was a yellow oil.

References