Hydrogen Peroxide → HCID 86653780, compound

Participants

Reaction Steps

1-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-3-butene (1.1 g, 2.85 mmol) in THF (15 mL) was treated with 9-BBN (560 mg, 4.27 mmol, 1.5 equiv.) at room temperature. After 2.5 h the clear colorless solution was treated with 2.5 M aqueous NaOH (6 mL, 15 mmol), was added followed by slow, dropwise addition of 35% w/w H2O2 (5 mL, 58.5 mmol). During addition, the internal reaction temperature was kept below 35° C. by ice bath immersion. The biphasic solution was stirred for 1.5 h at room temperature, 35 mL isopropyl acetate added and the layers separated. The aqueous phase was extracted 3×25 mL isopropyl acetate and the combined organics washed 2×25 mL saturated aqueous NaCl and dried over Na2SO4. Flash chromatography (gradient elution 10-60% EtOAc/heptane) yielded 741 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butan-1-ol as a clear colorless oil. M++H at 405 m/z;

Provenance & Evidence