1,2-Dimethoxyethane → 2-(4-Methylphenyl)furan

HRID 2229164Notes

Reaction equation

HRID 2229164 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:12]1[O:13][CH:14]=[CH:15][CH:16]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 2776190Furan, 2-bromo-

Product 1

HCID 113895372-(4-Methylphenyl)furan

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-tolylboronic acid (500 mg), 2-bromofuran, and tetrakis(triphenylphosphine)palladium (177 mg) were added to the mixture of 24 ml of dimethoxyethane and 15 ml of ethanol under nitrogen atmosphere. Additionally 1N sodium carbonate (12 ml) was added to the mixture and the resulting mixture was heated at reflux for 2 h. Water was added to the mixture and the mitture was extracted with diethyl ether. The organic layer was dried and the solvent was removed under reduced pressure. The residue was purified by the use of silica gel column chromatography to give 438 mg of 2-(4-tolyl)furan.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionthe mitture was extracted with diethyl ether
  4. customThe organic layer was dried
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by the use of silica gel column chromatography

Sources & evidence

ORD record
ord-cb2f632e8cff42fc9a9dd15db835d8a3
Source dataset
uspto-grants-2002_07
Patent number
US06420367B1

Reaction notes

Loading…