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

HRID 336344Notes

Reaction equation

HRID 336344 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].N#N.N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C1COCC1.O>[C:15]([Si:12]([CH3:14])([CH3:13])[O:3][CH2:2][CH2:1][OH:4])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 795ImidazoleHCID 947NitrogenHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethylene glycol (2.44 mL; 6.0 eq.) in dry THF (35 mL), under inert atmosphere (N2), were added imidazole (497 mg; 1.0 eq.) and a solution of tert-butyldimethylsilyl chloride (1.10 g; 1.0 eq.) in dry THF (35 mL). The reaction mixture was stirred at rt over the weekend. Water was added and THF was removed under vacuum. The residual aq. layer was extracted with EA (3×) and the combined org. layers were washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Hept/EA 100:0 to 60:40), as a colorless liquid (258 mg; 20% yield).

Workup

  1. customTHF was removed under vacuum
  2. extractionThe residual aq. layer was extracted with EA (3×)
  3. washlayers were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01eeeff9358447b8af89e11ab00cf739
Source dataset
uspto-grants-2014_11
Patent number
US08889676B2

Reaction notes

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