반응 #10031

반응 방정식

bis-trichloromethylcarbonate

N-methylformanilide

butyl vinyl ether

→

N-methyl-N-phenylaminoacrolein

용매

1,4-dioxane

1,4-dioxane

반응 조건

후처리

1. 1
   기타the solvent is evaporated under reduced pressure
2. 2
   workup.ADDITIONToluene (50 ml) and water (200 ml) are added
3. 3
   온도the mixture is cooled at about 5–10° C.
4. 4
   workup.ADDITIONby adding sodium hydroxide 15% aqueous solution (30 ml)
5. 5
   기타After separation of the phases
6. 6
   추출the aqueous layer is extracted twice with toluene (50 ml×2)
7. 7
   세척the combined organic layers are washed with water (50 ml)
8. 8
   기타evaporated 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
    기타is used for the next step of the synthesis without any further purification

실험 절차

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.

출처