Lithium Hydroxide → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid

HRID 460042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460042
[OH-].[Li+].C[O:4][C:5]([C:7]1[O:8][C:9]([CH3:26])=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH:11]=1)=[O:6]>O1CCCC1.CO>[C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]2[CH:11]=[C:7]([C:5]([OH:6])=[O:4])[O:8][C:9]=2[CH3:26])=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 588241734-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Produkt 1

HCID 7868594-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acidAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

1M Aqueous lithium hydroxide (18 mL) was added to solution of 4-(biphenyl-4-yloxymethyl)-5-methyl-furan-2-carboxylic acid methyl ester (17) (1 g) in tetrahydrofuran/methanol (2:1 by volume, 100 mL) and the mixture stirred at room temperature for 5 h. The solvent was removed in vacuo, the residue dissolved in water (20 mL) and the solution acidified to pH6 with aqueous dilute hydrochloric acid. The mixture was evaporated to dryness and the residue was purified by HPLC to afford compound 18 as a white solid (210 mg). LC/MS System B: Rt=4.80 mins, m/z=307 ((M−1) for C19H16O4).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (20 mL)
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-adede7104c1646fc96ab731ee9893133
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196089B2

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