Potassium Carbonate → Ethyl 5-phenylbenzofuran-2-carboxylate

HRID 2057967

Reaction equation

HRID 2057967 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 1A, 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, poured into 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 (1B), 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. additionpoured into 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-198325f99e0341759bfdc909f8e0367d
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Linked notes

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