Synthesis
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).
References
[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 39
[2] Patent: US9301951, 2016, B2. Location in patent: Page/Page column 125
[3] Chemistry - A European Journal, 2018, vol. 24, # 62, p. 16526 - 16531
[4] Patent: US2010/76029, 2010, A1. Location in patent: Page/Page column 35
[5] Patent: US2011/71196, 2011, A1. Location in patent: Page/Page column 18-19
