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

HRID 1177070

Reaktionsgleichung

Reaktionsgleichung von HRID 1177070
[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 14838669HCID 14838669, Verbindung

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-f18dbbf2800d41dcb6a3952f62647bed
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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