Hydrogen Peroxide → 3-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol

Participants

Reaction Steps

To a solution of 2-allyl-2-phenyltetrahydro-2H-pyran (700 mg, 3.46 mmol) in THF (7 mL) at 0° C. was added 1M borane tetrahydrofuran complex (1.730 mL, 1.730 mmol) dropwise, and the mixture was stirred overnight at room temperature. After cooling to 0° C., water (0.07 ml) was added to destroy the excess borane. After stirring for 10 mins, 3M NaOH (0.42 mL, 1.260 mmol) was added and stirred for 10 mins. Then 30% H2O2 (0.42 mL, 4.11 mmol) was added and the cooling bath was removed. It was refluxed for 1.5 hrs and cooled to room temperature. It was extracted with EtOAc (2×), and the combined extracts were washed with brine, dried over Na2SO4 and evaporated to give 3-(2-phenyltetrahydro-2H-pyran-2-yl)propan-1-ol as oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.11-7.44 (5 H, m), 3.66-3.81 (2 H, m), 3.48-3.59 (2 H, m), 2.22-2.37 (2 H, m), 1.35-1.89 (8 H, m).

Provenance & Evidence