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Ethylene Glycol → 2-(tert-Butyl(dimethyl)silyl)oxyethanol

HRID 218992
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HRID 218992 반응식
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[Si:7](Cl)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].P([O-])([O-])([O-])=O>C1COCC1>[Si:7]([O:3][CH2:2][CH2:1][OH:4])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 1061PhosphateHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

생성물 1

HCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol수율 67.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

Ethylene glycol (2.00 g) in anhydrous THF (60 ml) under nitrogen was treated portionwise with sodium hydride (60% dispersion in mineral oil, 1.29 g) and the mixture stirred at 20° C. for 45 min. Tert-butyl dimethylsilyl chloride (4.86 g) was added and the mixture stirred at 20° C. for 45 min. Phosphate buffer (60 ml, pH6.5) was added and the mixture stirred for 20 min before extracting with ether (60 ml). The organic layer was then washed with water (60 ml) and brine (60 ml), before drying over Na2SO4, filtering, and removing the solvent in vacuo. This was purified by flash chromatography on silica. Elution with 1:4 EtOAc/cyclohexane followed by solvent evaporation in vacuo gave the title compound (3.82 g). TSP+ve 194 MNH4+.

후처리

  1. stirringthe mixture stirred at 20° C. for 45 min
  2. stirringthe mixture stirred for 20 min
  3. extractionbefore extracting with ether (60 ml)
  4. washThe organic layer was then washed with water (60 ml) and brine (60 ml)
  5. dry with materialbefore drying over Na2SO4
  6. filtrationfiltering
  7. customremoving the solvent in vacuo
  8. customThis was purified by flash chromatography on silica
  9. washElution with 1:4 EtOAc/cyclohexane
  10. customfollowed by solvent evaporation in vacuo

출처 및 근거

ORD 기록
ord-b4b6a62c649948de851411454b33d47f
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198483B2

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