Reacción #46162

Ecuación de reacción

3-(3-Benzyloxyphenyl)-3-oxopropionate ethyl ester

isopropylamine

→

2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide

Rendimiento 108.9%

Disolventes

m-xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was refluxed
2. 2
   workup.STIRRINGAfter stirring
3. 3
   Temperaturarefluxing for 24 hours at room temperature
4. 4
   Extracciónthe organic layer was extracted with saturated sodium chloride and ethyl acetate
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   Otroresulting residue
8. 8
   Otrowas purified by column chromatography (ethyl acetate:hexane=1:2)

Procedimiento

3-(3-Benzyloxyphenyl)-3-oxopropionate ethyl ester (174.42 g, 584.47 mmol) was dissolved in m-xylene and the reaction mixture was refluxed while stirring for 30 min at 150° C. Then, isopropylamine (38 g, 642.92 mmol) was added dropwise to the mixture. After stirring and refluxing for 24 hours at room temperature, the organic layer was extracted with saturated sodium chloride and ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and resulting residue was purified by column chromatography (ethyl acetate:hexane=1:2) to obtain 2-(3-benzyloxybenzoyl)-N-isopropyl-3-phenylacryl amide (127.13 g, yield 70%) as yellow oil.

Fuente