Sodium Hydroxide → 2,4-Diphenyl-5-oxazolecarboxylic acid

HRID 585114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585114
C([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[C:11]1([C:9]2[O:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 9900703HCID 9900703, Verbindung

Produkt 1

HCID 98784592,4-Diphenyl-5-oxazolecarboxylic acidAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of the above-prepared 2,4-diphenyl-oxazole-5-carboxylic acid ethyl ester (500 mg, 1.70 mmole, 1.0 eq) in dioxane (6 ml) was treated with 2N NaOH (1.7 ml, 3.4 mmole, 2.0 eq) and the mixture stirred at room temperature overnight under nitrogen. The mixture was then partitioned between ethyl acetate and 2.0N HCl. The organic phase washed with 0.5N HCl and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 426 mg of the title compound as a crude yellow solid. The product was used directly in the next step, without purification.

Aufarbeitung

  1. customThe mixture was then partitioned between ethyl acetate and 2.0N HCl
  2. washThe organic phase washed with 0.5N HCl and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-34bdd2179d134574802be73d328d468a
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930116B2

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