Réaction #52995

Équation de réaction

4-amino-2-chlorobenzoic acid methyl ester

2,5-dimethoxytetrahydrofuran

→

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

Solvants

water

AcOH

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 2 h
3. 3
   Extractionextracted with EtOAc
4. 4
   LavageThe extract was washed with satd
5. 5
   SéchageNaHCO3 and brine, dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   AutreThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 5/1)

Mode opératoire

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+).

Source