Methanol → 6-Methoxy-1-benzofuran-2-carboxylic acid

HRID 717706

Reaktionsgleichung

Reaktionsgleichung von HRID 717706
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([O:12]CC)=[O:11])[O:9][C:5]=2[CH:4]=1.CO.[Li+].[OH-]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[O:9][C:5]=2[CH:4]=1

Komponenten

6

Edukt 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 11830962Ethyl 6-methoxybenzofuran-2-carboxylate

Produkt 1

HCID 9188636-Methoxy-1-benzofuran-2-carboxylic acidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of Product of Step B (0.25 g, 1.21 mmol) in a mixture of THF, MeOH and H2O (5 ml:2 ml:1 ml), LiOH (0.145 g, 6 mmol) in H2O (0.5 ml) was added and the mixture was stirred for 3 h at room temp. The solvents were distilled off and the residue was portioned between EtOAc (20 ml) and 1M HCl (2 ml). The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.21 g, 91%), as a colourless solid. 1H-NMR (DMSO-d6) 7.61 (d, 1H, J=8.67 Hz); 7.54 (s, 1H); 7.24 (d, 1H, J=1.59 Hz); 6.93 (dd, 1H, J=8.67, 2.4 Hz); 3.8 (s, 3H).

Aufarbeitung

  1. additionwas added
  2. distillationThe solvents were distilled off
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-24371ff142734ca1a8a5b30910cd56a1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193716B2

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