tert-BUTYL CHLORIDE → methyl 5-tert-butyl-1H-pyrrole-2-carboxylate

HRID 18931

Reaktionsgleichung

Reaktionsgleichung von HRID 18931
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:14](Cl)([CH3:17])([CH3:16])[CH3:15]>C(=S)=S>[C:14]([C:7]1[NH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][CH:8]=1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 10486tert-BUTYL CHLORIDEHCID 136930Methyl pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 18322360methyl 5-tert-butyl-1H-pyrrole-2-carboxylateAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of the methylpyrrole-2-carboxylate (1.0 g, 7.99 mmol) and aluminum trichloride (2.13 g, 16.0 mmol) was dissolved in carbon disulfide (20 mL) and stirred at 50° C. for 1 hour. Tert-butyl chloride (0.740 g, 7.99 mmol) in carbon disulfide (5 mL) was added in one portion and the mixture stirred at room temperature for an additional 20 hours. The reaction mixture was quenched with ice and extracted with dichloromethane. The solvent was removed under vacuum and the resulting solid was washed with cold hexane to afford 0.850 g of the expected methyl 5-tert-butyl-1H-pyrrole-2-carboxylate as a tan solid.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for an additional 20 hours
  2. customThe reaction mixture was quenched with ice
  3. extractionextracted with dichloromethane
  4. customThe solvent was removed under vacuum
  5. washthe resulting solid was washed with cold hexane

Quellen und Nachweise

ORD-Eintrag
ord-da6f722551a4427295029d5676767d32
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741479B2

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