Sodium Carbonate → 2-(3,5-Dimethoxy-4-methylphenyl)furan

HRID 512632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512632
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1)(=O)=O.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:17][O:16][C:9]1[CH:8]=[C:7]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[CH3:15]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2734357Furan-2-boronic acidHCID 866575033,5-Dimethoxy-4-methylphenyl trifluoromethanesulfonate

Produkt 1

HCID 584320242-(3,5-Dimethoxy-4-methylphenyl)furanAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3,5-dimethoxy-4-methylphenyl trifluoromethanesulfonate (0.50 g, 1.67 mmol) in DME (15 mL) was added 2-furylboronic acid (0.245 g, 2.2 mmol), LiCl (0.149 g, 3.5 mmol), 2 M aqueous Na2CO3 (1.8 mL, 3.6 mmol) and tetrakis(triphenylphosphine)palladium (0.098 g, 0.085 mmol) and the mixture was degassed as described previously. The reaction was heated at 80° C. under argon for 22 hrs. After cooling to room temperature, the reaction was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-25% Et2O-hexanes) gave 2-(3,5-dimethoxy-4-methylphenyl)furan as a white solid (0.28 g, 77% yield).

Aufarbeitung

  1. customthe mixture was degassed
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction was diluted with H2O
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with H2O, saturated aqueous NH4Cl, H2O and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (0-25% Et2O-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9533601fae1e44fdb8c62acc23e623b6
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102643B2

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