Carbon Dioxide → 4-(Dimethylamino)but-2-ynoic acid

HRID 276819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276819
C([Li])CCC.[CH3:6][N:7]([CH3:11])[CH2:8][C:9]#[CH:10].[C:12](=[O:14])=[O:13].O>CCCCCC.O1CCCC1.CO>[CH3:6][N:7]([CH3:11])[CH2:8][C:9]#[C:10][C:12]([OH:14])=[O:13]

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 962WaterHCID 81643N,N-DimethylpropargylamineHCID 178418339Butyllithium

Produkt 1

HCID 150797524-(Dimethylamino)but-2-ynoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyl lithium in hexane (96 mL, 2.5 M in n-hexane) was slowly added to 1-dimethylamino-2-propyne (20 g, 240 mmol) in 100 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 h at −78° C., then dry carbon dioxide was pass through the reaction overnight. The resulting solution was poured into water and washed with ethyl acetate. The aqueous layer was evaporated under reduced pressure to give the crude acid. The dry acid was dissolved in methanol, and the insoluble salt was removed via filtration. The filtrate was collected and dried in vacuo to give 15.6 g of 4-dimethylamino-but-2-ynoic acid: mass spectrum (m/e):M−H 126.

Aufarbeitung

  1. customthrough the reaction overnight
  2. washwashed with ethyl acetate
  3. customThe aqueous layer was evaporated under reduced pressure
  4. customto give the crude acid
  5. customthe insoluble salt was removed via filtration
  6. customThe filtrate was collected
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-550a887d60f9488fbc9e51663994a57f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355636B1

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