Triethylamine → 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethan-1-one

HRID 1257356Notes

Reaction equation

HRID 1257356 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>O1CCCC1>[Si:18]([O:10][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84873-HydroxyacetophenoneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 143614891-(3-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethan-1-oneYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (40 mL) of 3-acetylphenol (5.0 g, 37 mmol) in tetrahydrofuran were added triethylamine (7.7 mL, 55 mmol) and tert-butyldimethylsilylchloride (6.6 g, 44 mmol), and the mixture was stirred at room temperature overnight. After confirmation of the termination of the reaction by TLC, the resulting salt was removed. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=9/1) to give the title compound (9.4 g, 100%) as a colorless oil.

Workup

  1. customAfter confirmation of the termination of the reaction by TLC
  2. customthe resulting salt was removed
  3. customThe solvent was evaporated under reduced pressure
  4. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-c08da9b5f59544938d843df93d84b861
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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