Lithium Chloride → 5-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester

HRID 1643543

Reaktionsgleichung

Reaktionsgleichung von HRID 1643543
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([CH2:12][CH:13]=[CH2:14])[C:5]=1[OH:15].[Li+].[Cl-]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Cu+2].Cl[Pd]Cl>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:15][C:13]([CH3:14])=[CH:12][C:6]=2[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)=[O:16]

Komponenten

7

Edukt 2

HCID 433294Lithium ChlorideHCID 148386693-Allyl-2-hydroxy-5-methoxy-benzoic acid methyl ester

Produkt 1

HCID 595604655-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl esterAusbeute 100,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 8895Cupric acetateKatalysatorHCID 24290Palladium ChlorideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-allyl-2-hydroxy-5-methoxy-benzoic acid methyl ester (4b) (1.48 g, 6.66 mmol) in DMF (30 mL) was added Cu(OAc)2 (3.63 g, 19.98 mmol), LiCl (847 mg, 19.98 mmol) in H2O (1 mL) and PdCl2 (24 mg, 0.133 mmol). The reaction mixture was stirred at RT for 3 h, quenched with H2O (100 mL) and NH4OH (5 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 10-15% EtOAc/hexane to give colorless oil (1.48 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=2.53 Hz, 1 H) 7.17 (d, J=2.53 Hz, 1 H) 6.36 (s, 1 H) 4.00 (s, 3 H) 3.87 (s, 3 H) 2.51 (s, 3 H)

Aufarbeitung

  1. customquenched with H2O (100 mL) and NH4OH (5 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph
  7. washeluting with 10-15% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-acc340d7a3a844cf94629aad272434ef
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119624B2

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