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

HRID 638311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638311
[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

Komponenten

6

Edukt 3

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 12795049Methyl 1-(2-iodoethyl)-4-chloropyrrol-2-acetate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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:

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-b7dd588eb3e04fe9ad5a2d180d6585b6
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560699

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