Reaktion #2430

Reaktionsgleichung

Methyl(3-amino)benzoate

4-Pentenoyl chloride

4-pentenoic acid

thionyl chloride

→

oil

Ausbeute 32.0%

Methyl 3-(4-pentenoylamino)benzoate

Ausbeute 32.0%

Lösungsmittel

pyridine

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C
2. 2
   Sonstigeevaporated
3. 3
   Sonstigeazeotroped with DCM)
4. 4
   workup.ADDITIONwas added dropwise in DCM (3 ml)
5. 5
   SonstigeThe mixture was evaporated
6. 6
   Sonstigepartitioned between EtOAc and 1M HCl
7. 7
   WaschenThe organic portion was washed with 5% KHCO3 and brine
8. 8
   Filtrationfiltered (Whatman® 1PS, phase separator)
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was chromatographed (eluant 30% EtOAc in hexanes)

Vorschrift

Methyl(3-amino)benzoate (4.5 g, 29.8 mmol) was taken up in DCM (10 ml) and pyridine (1 ml) at 0° C. 4-Pentenoyl chloride (freshly prepared from 4-pentenoic acid (3.0 g, 29.97 mmol) and thionyl chloride (6.6 ml) at r.t. for 1 h, evaporated and azeotroped with DCM) was added dropwise in DCM (3 ml). The mixture was allowed to warm to r.t. and stirred overnight. The mixture was evaporated and partitioned between EtOAc and 1M HCl. The organic portion was washed with 5% KHCO3 and brine, filtered (Whatman® 1PS, phase separator), and evaporated. The residue was chromatographed (eluant 30% EtOAc in hexanes) to provide a colourless oil (2.20 g, 32%).

Quelle