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Water → methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylate

HRID 505821
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505821
[Cl:1][C:2]1[NH:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([N:3]1[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]1[Cl:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 66974443methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate

Produkt 1

HCID 68468834methyl 1-benzyl-2-chloro-5-phenyl-1H-pyrrole-3-carboxylateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A solution (7 M) of methyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate in DMF at 0° C. was treated with NaH (1.2 eq., 60% dispersion in mineral oil), and the suspension was stirred at RT for 30 min then it was treated with benzyl bromide (1.2 eq.). The reaction mixture was stirred at RT for 90 min then poured into water and extracted with AcOEt. The combined organic phase was washed with water and dried. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:8 AcOEt/petroleum ether) to afford the title compound (71%) as a solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT for 90 min
  2. extractionextracted with AcOEt
  3. washThe combined organic phase was washed with water
  4. customdried
  5. customEvaporation of the solvent
  6. customgave a residue that
  7. customwas purified by flash chromatography on silica gel (1:8 AcOEt/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-0b88e83c557848fea88c13f6fb24b3ee
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781431B2

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