Triethylamine → 2-((tert-Butyldiphenylsilyl)oxy)ethanol

HRID 1766897Notes

Reaction equation

HRID 1766897 reaction equation
C([O:4][CH2:5][CH2:6][OH:7])(=O)C.C(N(CC)CC)C.[C:15]([Si:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16]>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC.C(OCC)(=O)C>[Si:19]([O:4][CH2:5][CH2:6][OH:7])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10960Glycol monoacetateHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 151562692-((tert-Butyldiphenylsilyl)oxy)ethanolYield 57.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Commercially available 2-hydroxyethyl acetate (3.12 g, 30.0 mmol), triethylamine (4.6 ml, 33 mmol), and 4-(N,N-dimethylamino)pyridine (100 mg) were dissolved in dichloromethane (20 ml), then tert-butylchlorodiphenylsilane (8.65 g, 31.5 mmol) was added thereto at room temperature, and the mixture was stirred for 20 hours. The obtained solution was diluted with a mixed solvent of hexane-ethyl acetate (1:1), and then the resulting solution was washed with water and with an aqueous solution of sodium chloride. The solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in methanol (100 ml), and 28% sodium methoxide in methanol (3 ml) was added thereto at room temperature followed by stirring for 2 hours. The solvent was distilled off under reduced pressure, and the residue was partitioned between ethyl acetate and a phosphate buffer solution (pH 7), then the organic layer was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford the crude title compound (5.18 g, 57% gross yield) as a colorless oil.

Workup

  1. washthe resulting solution was washed with water and with an aqueous solution of sodium chloride
  2. dry with materialThe solution was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in methanol (100 ml)
  5. addition28% sodium methoxide in methanol (3 ml) was added
  6. customat room temperature
  7. stirringby stirring for 2 hours
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was partitioned between ethyl acetate
  10. washa phosphate buffer solution (pH 7), then the organic layer was washed with an aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2c92a1f1dbe746269cb5168d18e8933c
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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