Reacción #52995

Ecuación de reacción

4-amino-2-chlorobenzoic acid methyl ester

2,5-dimethoxytetrahydrofuran

→

2-chloro-4-(1-pyrrolyl)benzoic acid methyl ester

Disolventes

water

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 2 h
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe extract was washed with satd
5. 5
   SecadoNaHCO3 and brine, dried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated
8. 8
   OtroThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 5/1)

Procedimiento

A mixture of 4-amino-2-chlorobenzoic acid methyl ester (0.46 g) and 2,5-dimethoxytetrahydrofuran (0.33 mL) in AcOH (16 mL) was heated under reflux for 2 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The extract was washed with satd. NaHCO3 and brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 5/1) to yield 0.48 g of 2-chloro-4-(1-pyrrolyl)benzoic acid methyl ester. ESMS: m/z 236 (MH+).

Fuente