Sodium Hydroxide → 4'-Fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylic acid

HRID 494195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494195
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16]C)=[O:15])=[CH:10][C:9]=2[O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 69039439Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylate

Produkt 1

HCID 690396114'-Fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylic acidAusbeute 11,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl 4′-fluoro-2-(2-methoxyethoxy)-1,1′-biphenyl-4-carboxylate (D76) (494 mg) was treated with aq. 2M sodium hydroxide solution (2 ml) in ethanol (3 ml) at 90° C. overnight. After cooling, the ethanol was evaporated off and the residue dissolved in EtOAc and extracted with sat. aq. sodium bicarbonate solution. This was acidified to pH3 with 2M HCl and extracted with EtOAc which was dried over MgSO4 and concentrated in vacuo to give the title compound as a solid (55 mg). MS(ES): M-H+ 289.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe ethanol was evaporated off
  3. dissolutionthe residue dissolved in EtOAc
  4. extractionextracted with sat. aq. sodium bicarbonate solution
  5. extractionextracted with EtOAc which
  6. dry with materialwas dried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2d6bde3cad07401a9de0ebff325799d2
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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