Sodium Chloride → methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

HRID 67115Notes

Reaction equation

HRID 67115 reaction equation
I[CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]1[CH2:10][C:11]([O:13][CH3:14])=[O:12].[Cl-].[Na+]>CN(C)C=O>[Cl:9][C:7]1[CH:6]=[C:5]2[CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH2:2][CH2:3][N:4]2[CH:8]=1

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 12795049Methyl 1-(2-iodoethyl)-4-chloropyrrol-2-acetate

Product 1

HCID 12795078methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of argon, 2.52 g. of 50% sodium hydride in mineral oil (0.053 mol.) is washed free of the carrier with dry hexane (2×20 ml.). Thereafter 150 ml. of anhydrous dimethylformamide is added and the mixture is cooled to 0°. To this mixture is added, with stirring, 16.4 g. of methyl 1-(2-iodoethyl)-4-chloropyrrol-2-acetate (0.05 mol.) dissolved in 50 ml. dimethylformamide. The reaction mixture is left at room temperature for 2 hours, when saturated aqueous sodium chloride solution is added and the product extracted into benzene (3×200 ml.). The organic extract is washed with water (2×100 ml.), dried over sodium sulphate and evaporated in vacuo. The crude product (8.52 g.) is purified by column chromatography on silica gel (245 g.) using hexane-ethyl acetate (90:10) as the eluting solvent, to yield methyl 6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate, an oil having the following physical constants:

Workup

  1. washof 50% sodium hydride in mineral oil (0.053 mol.) is washed free of the carrier with dry hexane (2×20 ml.)
  2. additionof anhydrous dimethylformamide is added
  3. temperaturethe mixture is cooled to 0°
  4. additionTo this mixture is added
  5. extractionthe product extracted into benzene (3×200 ml.)
  6. extractionThe organic extract
  7. washis washed with water (2×100 ml.)
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. customThe crude product (8.52 g.) is purified by column chromatography on silica gel (245 g.)

Sources & evidence

ORD record
ord-3f8c0a8e973042a6bf0bc388e2922452
Source dataset
uspto-grants-1982_08
Patent number
US04344943

Reaction notes

Loading…