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

HRID 40551Notes

Reaction equation

[CH3:1][Si:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH:5]=[CH2:6])[CH:3]=[CH2:4].C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[OH2:33].[OH:34]O>C1COCC1>[OH:33][CH2:6][CH2:5][Si:2]([CH3:1])([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:3][CH2:4][OH:34]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperaturethe mixture is refluxed for 4 h
temperatureThe mixture is then refluxed for 2 h
extractionThe two-phase mixture is extracted with ethyl acetate three times
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe raw product obtained
customis chromatographed on silica gel
washeluting with a gradient of ethanol and of dichloromethane in heptane ranging from 0.4/3.6/6 to 0.4/4.4/5

Sources & evidence

ORD record: ord-032d3a205451434c827bd1545d6ede8f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530473B2

Reaction notes

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