Potassium Carbonate → 5-Phenyl-2-furaldehyde

HRID 896474

Reaktionsgleichung

Reaktionsgleichung von HRID 896474
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]1([C:2]2[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 6003285-Bromofuran-2-carbaldehyde

Produkt 1

HCID 27694205-Phenyl-2-furaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 5-bromo-furan-2-carbaldehyde (1.08 g, 6.16 mmol, 1 eq), phenylboronic acid (0.90 g, 7.39 mmol, 1.1 eq), tetrabutylammonium bromide (1.99 g, 6.16 mmol, 1 eq), palladium acetate (30 mg, 0.0.12 mmol 0.02 eq), K2CO3 (2.13 g, 15.4 mmol, 2.5 eq) in water (10 mL) is stirred under nitrogen at rt overnight. The reaction is diluted with 40 mL water and extracted with EtOAc (3×100 mL). The organic layers are combined and stirred with charcoal for 30 min, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure to give 5-phenyl-furan-2-carbaldehyde as an oil. The product is purified by silica gel chromatography using a Biotage Flash 40M column (10% EtOAc/heptane).

Aufarbeitung

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-98b5835f61b24615b76ebd54d47bdad3
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919359B2

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