Reacción #49025

Ecuación de reacción

ammonium chloride

4-bromo-n-butyric acid ethyl ester

N-hydroxyphthalimide

Hunig base

→

4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyric acid ethyl ester

Rendimiento 100.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe resultant mixture was extracted with ethyl acetate (3×40 ml)
2. 2
   LavadoThe combined organic layers were washed with saturated brine (2×30 ml)
3. 3
   Secadodried over Na2SO4
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe resultant residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate (2:1))

Procedimiento

To a solution of 4-bromo-n-butyric acid ethyl ester (1.2 g, 6.13 mmol) in dimethylformamide (9 ml) were added N-hydroxyphthalimide (1.5 g, 9.19 mmol) and Hunig base (N,N-diisopropylethylamine, 2.13 mL) at room temperature, and the mixture was stirred at 80° C. over night. The reaction mixture was poured into saturated aqueous ammonium chloride, and the resultant mixture was extracted with ethyl acetate (3×40 ml). The combined organic layers were washed with saturated brine (2×30 ml), dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate (2:1)) to give 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyric acid ethyl ester (1.47 g, 100%).

Fuente