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

HRID 40551ノート

反応式

HRID 40551 の反応式
[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]

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 594382Methylphenyldivinylsilane

生成物 1

HCID 676060772-[(2-Hydroxy-ethyl)-methyl-phenyl-silanyl]-ethyl alcohol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-032d3a205451434c827bd1545d6ede8f
出典データセット
uspto-grants-2013_09
特許番号
US08530473B2

反応ノート

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