Ethyl bromoacetate → Ethyl [4-tert-butyl-3-(2-methoxyethoxy)phenoxy]acetate

HRID 1350863Notes

Reaction equation

HRID 1350863 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])([CH3:6])([CH3:5])[CH3:4].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:9][C:8]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 210974934-tert-Butyl-3-(2-methoxyethoxy)phenol

Product 1

HCID 58640405Ethyl [4-tert-butyl-3-(2-methoxyethoxy)phenoxy]acetateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a tetrahydrofuran (THF) (10 ml) suspension of sodium hydride (60% in mineral oil) (68 mg, 1.7 mmol) was added a tetrahydrofuran (THF) solution (5 ml) of 4-tert-butyl-3-(2-methoxyethoxy)phenol (320 mg, 1.4 mmol) and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added ethyl bromoacetate (190 ul, 1.7 mmol) at ambient temperature. The stirred mixture was refluxed for 4 hours. The reaction mixture was then quenched with saturated aqueous solution of ammonium chloride and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with ethyl acetate/hexane=1/9 to furnish 0.26 g (60% yield) of the title compound as colorless oil.

Workup

  1. temperatureThe stirred mixture was refluxed for 4 hours
  2. customThe reaction mixture was then quenched with saturated aqueous solution of ammonium chloride
  3. extractioncrude products were extracted with ethyl acetate The organic layer
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customto separate solvent and sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto give a residue, which
  10. washeluted with ethyl acetate/hexane=1/9

Sources & evidence

ORD record
ord-0dcb985bd363465a90fd16cb44f82063
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

Loading…