Sodium hydride → 1-Benzyl-3-(2-methoxycarbonylvinyl)pyrrole

HRID 11235

Reaktionsgleichung

Reaktionsgleichung von HRID 11235
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)OCC)C.[CH2:16]([N:23]1[CH:27]=[CH:26][C:25]([CH:28]=O)=[CH:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:23]1[CH:27]=[CH:26][C:25]([CH:28]=[CH:11][C:12]([O:14][CH3:15])=[O:13])=[CH:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 156784801-Benzyl-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 691390211-Benzyl-3-(2-methoxycarbonylvinyl)pyrroleAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 311 mg, 7.8 mmol) in DMF (15 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (1.64 g, 7.8 mmol) in DMF (3 ml). The mixture was stirred for 30 minutes at room temperature and cooled again. To the mixture was added dropwise a solution of 1-benzyl-3-formylpyrrole (1.2 g, 6.5 mmol) in DMF (2 ml). The reaction mixture was stirred for 12 hours at room temperature and poured into ice-water, and extracted with ethylacetate. The extract was washed with water and dried. The solvent was evaporated. The obtained white crystal was washed with i-Pr2O to give 1-benzyl-3-(2-methoxycarbonylvinyl)pyrrole (1.3 g). Yield: 83%.

Aufarbeitung

  1. temperaturecooled again
  2. stirringThe reaction mixture was stirred for 12 hours at room temperature
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with water
  5. customdried
  6. customThe solvent was evaporated
  7. washThe obtained white crystal was washed with i-Pr2O

Quellen und Nachweise

ORD-Eintrag
ord-f8ffdd4a3dcd491a8cc70900384a71ec
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098201B2

Verknüpfte Notizen

Wird geladen…