Hydrogen Peroxide → 2-[(2-Hydroxy-ethyl)-methyl-phenyl-silanyl]-ethyl alcohol

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Reaction Conditions

Reaction Steps

16.1 g of methyl-phenyl-divinyl-silane is put in 65 ml of anhydrous THF under nitrogen at room temperature. 24.6 g of 9-BBN dimer is added and the mixture is refluxed for 4 h. On return to room temperature, 40 ml of H2O is added, followed by 90 ml of a 3N soda solution. The mixture is cooled to 0° C. and 90 ml of a 30% solution of hydrogen peroxide is added cautiously. The mixture is then refluxed for 2 h. The two-phase mixture is extracted with ethyl acetate three times. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated under vacuum. The raw product obtained is chromatographed on silica gel, eluting with a gradient of ethanol and of dichloromethane in heptane ranging from 0.4/3.6/6 to 0.4/4.4/5. 15.1 g of 2-[(2-hydroxy-ethyl)-methyl-phenyl-silanyl]-ethyl alcohol is obtained in the form of a white solid.

Provenance & Evidence