Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate → 1-[(4-chlorophenyl)methyl]-1H-pyrrole-2-carboxylic acid

HRID 83593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83593
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1

Komponenten

4

Edukt 1

HCID 50900833Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate

Produkt 1

HCID 41200551-[(4-chlorophenyl)methyl]-1H-pyrrole-2-carboxylic acidAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate (550 mg, 2.203 mmol) was dissolved in ethanol (10 mL) and 7M aq. NaOH (8 mL). The reaction was stirred at 70° C. for 4 h and allowed to cool for 1 h. The ethanol was stripped by rotary evaporation until material began to precipitate, at which point the aqueous mixture was cooled in an ice bath and acidified with conc. HCl, which elicited further precipitation. The precipitate was collected over a filter and washed with a small amount of cold 1M HCl and dried under high vacuum to provide 375 mg of the title compound as a white, powdery solid.

Aufarbeitung

  1. temperatureto cool for 1 h
  2. customThe ethanol was stripped by rotary evaporation until material
  3. customto precipitate, at which point the aqueous mixture
  4. temperaturewas cooled in an ice bath
  5. customprecipitation
  6. customThe precipitate was collected over
  7. filtrationa filter
  8. washwashed with a small amount of cold 1M HCl
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b185ba63cbe54d82a958d1e15353d285
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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