Potassium Carbonate → Ethyl 5-phenylbenzofuran-2-carboxylate

HRID 2057958Notes

Reaction equation

HRID 2057958 reaction equation
[C:1]1([C:7]2[CH:14]=[C:11]([CH:12]=O)[C:10]([OH:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:17](C(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:15][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][C:11]=3[CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

Product 1

HCID 20329644Ethyl 5-phenylbenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.99 g of 5A, 0.96 g of diethyl bromomalonate and 1.25 g of anhydrous potassium carbonate in 20 ml of 2-butanone, was refluxed for 10 hours. The solvent was evaporated under reduced pressure. The residue was cooled, mixed with 100 ml of water and extracted with ether. The extract was washed with cold 5% sodium hydroxide solution and water and then concentrated under reduced pressure. The residue was recrystallized from ethanol to give ethyl 5-phenylbenzofuran-2-carboxylate (10B), as white crystals, mp: 109°-110° C.

Workup

  1. temperaturewas refluxed for 10 hours
  2. customThe solvent was evaporated under reduced pressure
  3. temperatureThe residue was cooled
  4. additionmixed with 100 ml of water
  5. extractionextracted with ether
  6. washThe extract was washed with cold 5% sodium hydroxide solution and water
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-61be619ad6454a789e1fecfc9e130eae
Source dataset
uspto-grants-1980_07
Patent number
US04213999

Reaction notes

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