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

HRID 1875284Notes

Reaction equation

HRID 1875284 reaction equation
C1COCC1.[H-].[Na+].[CH2:8]([OH:11])[CH2:9][OH:10].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(OCC)C>[Si:12]([O:10][CH2:9][CH2:8][OH:11])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

154 ml of dry THF and 1.88 g NaH are stirred under in a nitrogen atmosphere in a 500 ml round bottom flask condenser. 4.4 mL dry ethylene glycol are added into the flask, resulting in a large precipitate after 45 minutes of stirring. 11.8 g tert-butyldimethylsilyl chloride is added to the flask and vigorous stirring is continued for 45 minutes. The resulting mixture is poured into 950 mL ethylether. The ether is washed with 420 mL brine and solution is dried with sodium sulfate. The product is concentrated by evaporation of the ether in vacuo and purified by flash chromatography using a 27×5.75 cm column charged with silica gel using a hexanes/Et2O (75:25 v/v) solvent system. The product is stored at 0° C.

Workup

  1. customresulting in a large precipitate after 45 minutes
  2. stirringvigorous stirring
  3. washThe ether is washed with 420 mL brine and solution
  4. dry with materialis dried with sodium sulfate
  5. concentrationThe product is concentrated by evaporation of the ether in vacuo
  6. custompurified by flash chromatography
  7. additioncharged with silica gel using a hexanes/Et2O (75:25 v/v) solvent system
  8. customis stored at 0° C.

Sources & evidence

ORD record
ord-92b6faa9e79f489d8d500f2a1aeadafe
Source dataset
uspto-grants-2012_11
Patent number
US08308795B2

Reaction notes

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