Reaktion #162722

Reaktionsgleichung

acetic acid

ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-oxopropanoate

2-aminoethanol

→

title compound

Ausbeute 98.2%

(Z)-Ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate

Ausbeute 98.2%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated in vacuo
3. 3
   SonstigeThe residue was partitioned between EtOAc and water
4. 4
   EinengenThe organic layer was concentrated in vacuo
5. 5
   Sonstigethe crude material was purified by chromatography on silica eluting with 20-80% EtOAc/heptane

Vorschrift

To a solution of ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-oxopropanoate (500 mg, 1.97 mmol) in EtOH (4 mL) was added 2-aminoethanol (0.60 mL, 9.9 mmol) followed by acetic acid (0.63 mL, 9.9 mmol). The reaction mixture was heated to 90° C. for 16 hours, cooled to room temperature and concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic layer was concentrated in vacuo and the crude material was purified by chromatography on silica eluting with 20-80% EtOAc/heptane to provide the title compound (573 mg, 98%) as a clear gum.

Quelle