Реакция #1375838

Уравнение реакции

N-(4-Methylthiophenyl)alanine ethyl ester

n-butyl iodide

potassium carbonate

→

ester

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

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураat reflux for 48 h under a nitrogen atmosphere
3. 3
   ТемператураThe reaction mixture was cooled
4. 4
   Другоеpartitioned between 300 mL ethyl acetate and 200 mL brine
5. 5
   ДругоеThe organic layer was separated
6. 6
   Промывкаwashed with 100 mL brine
7. 7
   Другоеdried over anhyd
8. 8
   Концентрированиеsodium sulfate, and concentrated at reduced pressure
9. 9
   workup.ADDITIONThe resulting oil was charged onto a silica gel column
10. 10
    Промывкаeluted with heptane:THF (5:1)

Методика

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%).

Источник