Diethyl Ether → 3-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid

HRID 467745

Reaktionsgleichung

Reaktionsgleichung von HRID 467745
C([O:3][C:4]([C:6]1[C:7]([C:11](=[O:16])[NH:12][CH:13]2[CH2:15][CH2:14]2)=[N:8][O:9][CH:10]=1)=[O:5])C.[Li+].[OH-].C(OCC)C>C1COCC1.C(O)C>[CH:13]1([NH:12][C:11]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=2)=[O:16])[CH2:14][CH2:15]1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 700979003-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 700967853-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acidAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 3-(cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester (600 mg, 2.68 mmol) in THF (7 ml) and ethanol (3 ml) was added LiOH (1M; 5.35 ml, 5.35 mmol) at 0-5° C. The mixture was stirred at 20° C. for 1 h, poured into 50 ml diethyl ether and extracted. The organic phase was washed with water. The combined aqueous phases were acidified with 1M HCl (6 ml) and extracted with dichloromethane. The organic layers were dried and evaporated to yield the product as yellow oil (464 mg, 80%).

Aufarbeitung

  1. extractionextracted
  2. washThe organic phase was washed with water
  3. extractionextracted with dichloromethane
  4. customThe organic layers were dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cb1f1ea9fee24a9fab4b5e788f07155c
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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