反応 #1375838

反応方程式

N-(4-Methylthiophenyl)alanine ethyl ester

n-butyl iodide

potassium carbonate

→

ester

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

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux for 48 h under a nitrogen atmosphere
3. 3
   温度The reaction mixture was cooled
4. 4
   その他partitioned between 300 mL ethyl acetate and 200 mL brine
5. 5
   その他The organic layer was separated
6. 6
   洗浄washed with 100 mL brine
7. 7
   その他dried over anhyd
8. 8
   濃縮sodium sulfate, and concentrated at reduced pressure
9. 9
   workup.ADDITIONThe resulting oil was charged onto a silica gel column
10. 10
    洗浄eluted with heptane:THF (5:1)

実験手順

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%).

出典