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

HRID 638311Notes

Reaction equation

HRID 638311 reaction equation
[H-].[Na+].I[CH2:4][CH2:5][N:6]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]1[CH2:12][C:13]([O:15][CH3:16])=[O:14].[Cl-].[Na+]>CCCCCC.CN(C)C=O>[Cl:11][C:9]1[CH:8]=[C:7]2[CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:4][CH2:5][N:6]2[CH:10]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 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 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

In an atmosphere of argon, 2.52 g of 50% sodium hydride in mineral oil (0.053 moles) 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 moles) 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. temperaturethe mixture is cooled to 0°
  2. additionTo this mixture is added
  3. extractionthe product extracted into benzene (3×200 ml)
  4. extractionThe organic extract
  5. washis washed with water (2×100 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. customThe crude product (8.52 g) is purified by column chromatography on silica gel (245 g)

Sources & evidence

ORD record
ord-b7dd588eb3e04fe9ad5a2d180d6585b6
Source dataset
uspto-grants-1985_12
Patent number
US04560699

Reaction notes

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