Ammonium Hydroxide → 4-(Thiophen-3-yl)butanoic acid

HRID 1517042

Reaktionsgleichung

Reaktionsgleichung von HRID 1517042
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH:8](C(O)=O)[C:9]([OH:11])=[O:10])=[CH:2]1.[OH-].[NH4+]>COCCOCCOC>[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:2]1

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 54550536[2-(Thiophen-3-yl)ethyl]propanedioic acid

Produkt 1

HCID 110411434-(Thiophen-3-yl)butanoic acidAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

The product from Step C (2.4 g, 11.0 mmol) was dissolved in 2-methoxyethyl ether (20 mL) and refluxed for 24 hours. The reaction was cooled to room temperature and basified to pH 9 with concentrated ammonium hydroxide. The mixture was extracted once with diethyl ether and set aside. The aqueous layer was acidified with concentrated hydrochloride acid and extracted four times with diethyl ether. The extract were combined and dried over sodium sulfate, filtered and concentrated to give 4-thiophen-3-yl-butyric acid (1.8 g, 95%) as an oil.

Aufarbeitung

  1. temperaturerefluxed for 24 hours
  2. extractionThe mixture was extracted once with diethyl ether
  3. extractionextracted four times with diethyl ether
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b013f66cb3bf42249f49096a9bf2b275
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227486B2

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