反応 #10031

反応方程式

bis-trichloromethylcarbonate

N-methylformanilide

butyl vinyl ether

→

N-methyl-N-phenylaminoacrolein

溶媒

1,4-dioxane

1,4-dioxane

反応条件

後処理

1. 1
   その他the solvent is evaporated under reduced pressure
2. 2
   workup.ADDITIONToluene (50 ml) and water (200 ml) are added
3. 3
   温度the mixture is cooled at about 5–10° C.
4. 4
   workup.ADDITIONby adding sodium hydroxide 15% aqueous solution (30 ml)
5. 5
   その他After separation of the phases
6. 6
   抽出the aqueous layer is extracted twice with toluene (50 ml×2)
7. 7
   洗浄the combined organic layers are washed with water (50 ml)
8. 8
   その他evaporated under reduced pressure
9. 9
   workup.ADDITIONThe obtained residue (32.3 g, containing, according to HPLC assay, 28.7 g of pure product, 81% molar yield)
10. 10
    その他is used for the next step of the synthesis without any further purification

実験手順

To a solution of N-methylformanilide (30 g), butyl vinyl ether (22.2 g) in 25 ml of 1,4-dioxane under stirring at 10–15° C., a solution of bis-trichloromethylcarbonate (28.3 g) in 50 ml of 1,4-dioxane is added dropwise in 90 min. The reaction mixture is kept under stirring at room temperature overnight, then the solvent is evaporated under reduced pressure. Toluene (50 ml) and water (200 ml) are added, the mixture is cooled at about 5–10° C. and the pH is corrected to about 7 by adding sodium hydroxide 15% aqueous solution (30 ml). After separation of the phases, the aqueous layer is extracted twice with toluene (50 ml×2) and the combined organic layers are washed with water (50 ml) and evaporated under reduced pressure. The obtained residue (32.3 g, containing, according to HPLC assay, 28.7 g of pure product, 81% molar yield) is used for the next step of the synthesis without any further purification.

出典