Carbon Dioxide → 4-[(2-Methoxy-ethyl)-methyl-amino]-but-2-ynoic acid

HRID 1595709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595709
C([Li])CCC.[CH3:6][O:7][CH2:8][CH2:9][N:10]([CH3:14])[CH2:11][C:12]#[CH:13].[C:15](=[O:17])=[O:16].O>CCCCCC.O1CCCC1.CO>[CH3:6][O:7][CH2:8][CH2:9][N:10]([CH3:14])[CH2:11][C:12]#[C:13][C:15]([OH:17])=[O:16]

Komponenten

8

Edukt 4

HCID 280Carbon DioxideHCID 962WaterHCID 18548974(2-Methoxyethyl)(methyl)(prop-2-yn-1-yl)amineHCID 178418339Butyllithium

Produkt 1

HCID 185489684-[(2-Methoxy-ethyl)-methyl-amino]-but-2-ynoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyl lithium in hexane (37.8 mL, 2.5 M in n-hexane) was slowly added to (2-methoxy-ethyl)-methyl-prop-2-ynyl-amine (12.0 g, 94.5 mmol) in 90 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 hr at −78° C., then dry carbon dioxide was passed through 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 g of 4-[(2-methoxy-ethyl)-methyl-amino]-but-2-ynoic acid: mass spectrum (m/e): M−H 170.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3df101e14cb64534a300c0594e12a0f6
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288082B1

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