Reaktion #1375838

Reaktionsgleichung

N-(4-Methylthiophenyl)alanine ethyl ester

n-butyl iodide

potassium carbonate

→

ester

N-(4-Methylthiophenyl)-N-(n-butyl)alanine ethyl ester

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux for 48 h under a nitrogen atmosphere
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Sonstigepartitioned between 300 mL ethyl acetate and 200 mL brine
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with 100 mL brine
7. 7
   Sonstigedried over anhyd
8. 8
   Einengensodium sulfate, and concentrated at reduced pressure
9. 9
   workup.ADDITIONThe resulting oil was charged onto a silica gel column
10. 10
    Wascheneluted with heptane:THF (5:1)

Vorschrift

N-(4-Methylthiophenyl)alanine ethyl ester (10.0 g, 42.0 mmol), n-butyl iodide (7.9 g, 42 mmol) and potassium carbonate were added to 150 mL of acetonitrile and the mixture was heated at reflux for 48 h under a nitrogen atmosphere. The reaction mixture was cooled and then partitioned between 300 mL ethyl acetate and 200 mL brine. The organic layer was separated, washed with 100 mL brine, dried over anhyd. sodium sulfate, and concentrated at reduced pressure. The resulting oil was charged onto a silica gel column and eluted with heptane:THF (5:1). The desired ester was isolated as a yellow oil (3.0 g, 24%).

Quelle