Water → HCID 53678401, compound

HRID 1977702Notes

Reaction equation

HRID 1977702 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][C:13](=[O:15])[CH3:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O.[CH3:24]C(O)C>>[CH:21]([O:20][C:18](=[O:19])[CH2:17][CH:12]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=1)[C:13](=[O:15])[CH3:14])([CH3:22])[CH3:24]

Participants

6

Reactant 5

HCID 962WaterHCID 3776Isopropanol3×HCID 7748Ethyl bromoacetateHCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 5360545Sodium

Product 1

HCID 53678401HCID 53678401, compound

Conditions

Temperature
0 °C

Procedure

0.12 g (5.30 mM) sodium was dissolved in 5 ml of 2-propanol and the resultant solution was stirred over night at room temperature. 1.00 g (5.15 mM) of 3,4-dimethoxyphenylacetone dissolved in 1 ml of 2-propanol was dropwise added to the solution. The solution was cooled to 0° C. 0.89 g (5.30 mM) of ethyl bromoacetate dissolved in 1 ml of 2-propanol was dropwise added to the solution, and the mixture was stirred for about 2 hours at that temperature. The solution obtained was poured to water and the resultant product was extracted with methylene chloride. The organic extract was dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to obtain a yellow oily crude product. The crude product was purified by chromatography (SiO2: eluted with a gradient of 20% methyl acetate/hexane to 25% methyl acetate/hexane). The solvent was evaporated in vacuo and was dried to obtain 0.67 g of colorless 3-(3,4-dimethoxyphenyl)4-oxovaleric acid isopropyl ester.

Workup

  1. additionwas dropwise added to the solution
  2. additionwas dropwise added to the solution
  3. customThe solution obtained
  4. extractionthe resultant product was extracted with methylene chloride
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customto obtain a yellow oily crude product
  9. customThe crude product was purified by chromatography (SiO2
  10. washeluted with a gradient of 20% methyl acetate/hexane to 25% methyl acetate/hexane)
  11. customThe solvent was evaporated in vacuo
  12. customwas dried

Sources & evidence

ORD record
ord-23069b316eb6479a9047e93f7f5e6880
Source dataset
uspto-grants-2001_05
Patent number
US06235739B1

Reaction notes

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