Reaktion #466332

Reaktionsgleichung

water

n-Butyl lithium

bis-(2-methoxy-ethyl)-prop-2-ynyl-amine

carbon dioxide

→

4-[bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid

Lösungsmittel

hexane

tetrahydrofuran

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with ethyl acetate
2. 2
   SonstigeThe aqueous layer was evaporated under reduced pressure
3. 3
   Sonstigeto give the crude acid
4. 4
   Sonstigethe insoluble salt was removed via filtration
5. 5
   SonstigeThe filtrate was collected
6. 6
   Sonstigedried in vacuo

Vorschrift

n-Butyl lithium in hexane (42 mL, 2.5M in n-hexane) was slowly added to bis-(2-methoxy-ethyl)-prop-2-ynyl-amine (18 g, 105 mmol) in 80 mL of tetrahydrofuran under nitrogen. The mixture was stirred for 1 h 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 18 g of 4-[bis-(2-methoxy-ethyl)-amino]-but-2-ynoic acid: mass spectrum (m/e): M−H 214.

Quelle