Potassium Carbonate → HCID 19080364, compound

HRID 865522Notes

Reaction equation

HRID 865522 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])[CH:2]([CH3:4])[CH3:3].Br[CH:17]([C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([C:5]1[CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[CH:12]=[CH:13][C:14]=1[O:15][CH:17]([C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetateHCID 19080443HCID 19080443, compound

Product 1

HCID 19080364HCID 19080364, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.008 g (4.84 mmol) of methyl 3-iso-butyl-4-hydroxybenzoate and 1.737 g (6.05 mmol) of ethyl α-bromo-3,4-methylenedioxyphenylacetate in 10 mL of acetone was added 1.338 g (10 mmol) of finely powdered potassium carbonate. The reaction mixture was magnetically stirred and refluxed for 4 hours, then cooled to room temperature, filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 10% EtOAc-hexane; combination of the purified fractions and drying in vacuo afforded 1.518 g (76%) of the title compound as an amorphous powder.

Workup

  1. temperaturerefluxed for 4 hours
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was purified on a silica gel flash chromatography column
  5. washeluted with 10% EtOAc-hexane
  6. customcombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-9f5f3b182c6f4461b1f1ca4f0e0b6ce5
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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