Tetrahydro-4-pyranol

29943-42-8

2081-44-9

General procedure for the synthesis of tetrahydropyran-4-ol from tetrahydropyranone: To a tetrahydrofuran (THF, 25 mL) solution of tetrahydropyranone (5.0 g, 50 mmol), which was cooled to 0 °C, a THF (50 mL) suspension of lithium aluminum hydride (LiAlH4, 3.8 g, 0.1 mol) was slowly added. The reaction mixture was stirred at 0 °C for 30 min, followed by sequential addition of water (3.8 mL), 15% aqueous sodium hydroxide (NaOH) solution (3.8 mL) and water (11.4 mL) to quench the reaction. The mixture was filtered and the solid was washed with ethyl acetate (70 mL x 2). The filtrates were combined and evaporated to give tetrahydropyran-4-ol (5.09 g, 99% yield).