Potassium Carbonate → HCID 10130413, compound

HRID 1937040Notes

Reaction equation

HRID 1937040 reaction equation
Cl[C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:6]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+]>C(OCCCC)CCC>[C:11]1([C:2]2[O:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 22463309Methyl 5-chloro-3-furancarboxylate

Product 1

HCID 10130413HCID 10130413, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

50 mmol of methyl 2-chlorofuran-4-carboxylate were heated with 52 mmol of phenylboronic acid, 50 mmol of potassium carbonate, 25 mmol of lithium chloride and 0.25 mmol of trans-di-μ-acetato-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium (1 mol %) in 150 ml of dibutylether at 80° C. for 8 hours. Aqueous work-up, filtration through a short silica gel column and distilling off the solvent leaves methyl 2-phenylfuran-4-carboxylate as a colorless residue. Yield: 85%.

Workup

  1. filtrationAqueous work-up, filtration through a short silica gel column
  2. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-0e9142ae7dd94c8f8194f88f1ae6753b
Source dataset
uspto-grants-2002_05
Patent number
US06392047B1

Reaction notes

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