Sodium Iodide → methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate
Reaction equation
S(O[CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[C:9]1[CH2:17][C:18]([O:20][CH3:21])=[O:19])(C)(=O)=O.[I-:22].[Na+]>C(#N)C>[I:22][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][C:10]([C:13]([O:15][CH3:16])=[O:14])=[C:9]1[CH2:17][C:18]([O:20][CH3:21])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 785 mg of methyl N-(2-mesyloxyethyl)-3-carbomethoxypyrrole-2-acetate and 1.83 g of sodium iodide in 10 ml of acetonitrile is refluxed for 1 hour. The cooled reaction mixture is evaporated to dryness under reduced pressure and the residue is triturated with water. The insoluble material is separated by filtration and is air dried, thus obtaining 840 mg (97%) of methyl N-(2-iodoethyl)-3-carbomethoxypyrrole-2-acetate (VI, R=H), m.p. 137°-138° C.