Methanol → 5-Chloro-2-phenyl-oxazole-4-carboxylic acid

HRID 2236174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236174
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:9][C:10]=1[Cl:11])=[O:5])C.O1CCCC1.CO.[H-].[OH-].[Li+]>O>[Cl:11][C:10]1[O:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][C:6]=1[C:4]([OH:5])=[O:3]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 67537623Ethyl 5-chloro-2-phenyloxazole-4-carboxylateHCID 86597229HCID 86597229, Verbindung

Produkt 1

HCID 593012785-Chloro-2-phenyl-oxazole-4-carboxylic acidAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Solution of 5-chloro-2-phenyl-oxazole-4-carboxylic acid ethyl ester (92 mg, 0.37 mmol) in a mixture solution of tetrahydrofuran, methanol and water (3:1:1, 5 mL) was treated with lithium hydroxide monohydride (44 mg, 1.1 mmol) at room temperature for two hours. After the reaction was complete, solvent was evaporated. To the residue, water was added, and pH value of the aqueous layer was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N). The white precipitation was collected by centrifugation to give 5-chloro-2-phenyl-oxazole-4-carboxylic acid (73 mg, 88%). LCMS calcd for C10H6ClNO3 (m/e) 223, obsd 224 (M+H).

Aufarbeitung

  1. customsolvent was evaporated
  2. additionTo the residue, water was added
  3. additionpH value of the aqueous layer was adjusted to ˜1-2 by addition of dilute hydrochloride acid (1N)
  4. customThe white precipitation
  5. customwas collected by centrifugation

Quellen und Nachweise

ORD-Eintrag
ord-57305864de79446c80ea34b5949efd85
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714126B2

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