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

HRID 11234

Reaktionsgleichung

Reaktionsgleichung von HRID 11234
[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][CH:25]=[C:24]1[CH:28]=O)[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][CH:25]=[C:24]1[CH:28]=[CH:11][C:12]([O:14][CH3:15])=[O:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 111269641-benzyl-1H-pyrrole-2-carbaldehyde

Produkt 1

HCID 691390871-Benzyl-2-(2-methoxycarbonylvinyl)pyrroleAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% in mineral oil, 960 mg, 24 mmol) in DMF (20 ml) was added dropwise at an ice bath temperature a solution of diethyl(methoxycarbonylmethyl)phosphonate (5.04 g, 24 mmol) in DMF (1 ml). The mixture was stirred for 15 minutes at room temperature and cooled again. To the mixture was added dropwise a solution of 1-benzyl-2-formylpyrrole (3.7 g, 20 mmol) in DMF (2 ml). The reaction mixture was stirred for 4 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 isopropylether to give 1-benzyl-2-(2-methoxycarbonylvinyl)pyrrole (3.14 g). Yield. 65%.

Aufarbeitung

  1. temperaturecooled again
  2. stirringThe reaction mixture was stirred for 4 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 isopropylether

Quellen und Nachweise

ORD-Eintrag
ord-69dcbe63ba36463aa189ba6520443fe6
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098201B2

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