Water → Ethyl 2-(3,4,5-trimethoxyphenyloxy)-acetoacetate

HRID 720366Notes

Reaction equation

HRID 720366 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CC(C)([O-])C.[K+].Cl[CH:21]([C:27]([CH3:29])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>CN(C=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([O:13][CH:21]([C:27]([CH3:29])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11858Ethyl 2-chloroacetoacetateHCID 695053,4,5-TrimethoxyphenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 21891584Ethyl 2-(3,4,5-trimethoxyphenyloxy)-acetoacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4,5-Trimethoxyphenol (5,83 g) was dissolved in DMF (60 mL), and potassium tert-butoxide (3.55 g) was added to the solution under ice cooling. Ethyl 2-chloroacetoacetate (4.46 mL) was then added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was heated to 80° C. and stirred for 2 hours. After allowing the reaction mixture to cool, water was added to the reaction mixture to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3) to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was heated to 80° C.
  2. stirringstirred for 2 hours
  3. temperatureto cool
  4. extractionextraction with ethyl acetate
  5. washThe resultant organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-a2b04001b83e4e52b82b35da969c028e
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Reaction notes

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