Diethylene Glycol → 2-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol

HRID 1358880

Reaction equation

HRID 1358880 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[H-].[Na+].[Cl-].[CH3:11][SiH:12]([CH3:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[CH3:14][C:13]([Si:12]([CH3:17])([CH3:11])[O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 24758Sodium hydrideHCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanolYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20 g of diethyleneglycol is added to 9.05 g of sodium hydride in 320 cm3 of tetrahydrofuran, the reaction medium is agitated for 45 minutes, 28.3 g of dimethylterbutylsilane chloride is added, agitation is carried out for 3 hours while leaving the temperature to return to ambient. Extraction is carried out with ether, followed by washing with an aqueous solution of sodium bicarbonate, with salt water, drying and evaporating the solvent. 40.25 g of expected product is obtained.

Workup

  1. waitagitation is carried out for 3 hours
  2. customwhile leaving the temperature
  3. extractionExtraction
  4. washby washing with an aqueous solution of sodium bicarbonate, with salt water
  5. customdrying
  6. customevaporating the solvent

Sources & evidence

ORD record
ord-90299c7a679946a99270dd0793685b67
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Linked notes

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