Potassium Carbonate → HCID 18950593, compound

HRID 1492639Notes

Reaction equation

HRID 1492639 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH2:11][CH:12]=[CH2:13])[C:9]=1[OH:10])[CH2:5][OH:6].Br[CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([CH2:11][CH:12]=[CH2:13])[C:9]=1[O:10][CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 54390314HCID 54390314, compound

Product 1

HCID 18950593HCID 18950593, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a magnetically stirred solution of 0.545 g (2.74 mmol) of the product of Step B in 10 mL acetone was added 0.628 g (2.74 mmol) of methyl α-bromophenylacetate, 0.757 g (5.48 mmol) of potassium carbonate and the reaction mixture was heated at reflux for 2.5 hours. The reaction mixture was cooled to room temperature, filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 15% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.789 g (83%) of the title compound.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on a silica gel flash chromatography column
  6. washeluted with 15% EtOAc-hexane
  7. customEvaporation of the purified fractions
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-6fb53983d20e483e8d4aca04a1b11130
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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