Reaction #3663

Reaction equation

hydrogen peroxide

ethyl iodoacetate

hydrogen peroxide

1-(2-nitrophenyl)pyrrole

ethyl iodoacetate

→

product

Yield 10.9%

1-(2-Nitrophenyl)-2-pyrroleacetic acid, ethyl ester

Yield 10.9%

Solvents

water

dimethyl sulfoxide

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   workup.STIRRINGthe mixture stirred at room temperature for 1 day
3. 3
   Extractionextracted with diethyl ether
4. 4
   ExtractionThe organic extract
5. 5
   Washis washed with water, brine
6. 6
   Dryingdried (Na2SO4)
7. 7
   OtherThe solvent is removed
8. 8
   Otherthe residue (2.12 g) chromatographed on silica gel with ethyl acetate-hexane (1:4) as solvent

Procedure

To a stirred mixture of 1.88 g of 1-(2-nitrophenyl)pyrrole, 4.80 g of ethyl iodoacetate and 2.22 g of FeSO4.7H2O in 40 ml of dimethyl sulfoxide is added dropwise 10 ml of 30% hydrogen peroxide while keeping the reaction mixture at room temperature with a cold water bath. The mixture is stirred at room temperature for one day. An additional 2.4 g of ethyl iodoacetate, 1.1 g of FeSO4.7H2O and 5 ml of 30% hydrogen peroxide is added and the mixture stirred at room temperature for 1 day. The mixture is diluted with water and extracted with diethyl ether. The organic extract is washed with water, brine and dried (Na2SO4). The solvent is removed and the residue (2.12 g) chromatographed on silica gel with ethyl acetate-hexane (1:4) as solvent to give 0.30 g of product as a brown gum.

Source