Potassium Hydroxide → 2-Methyl-1-phenyl-pyrrole

HRID 880455

Reaktionsgleichung

Reaktionsgleichung von HRID 880455
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O.NN>C(O)CO>[CH3:12][C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 9347291-phenyl-1H-pyrrole-2-carbaldehyde

Produkt 1

HCID 46530262-Methyl-1-phenyl-pyrroleAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

A mixture of 1-phenylpyrrole-2-carbaldehyde (700 mg, 4.1 mmol), potassium hydroxide (490 mg, 12.3 mmol) and hydrazine hydrate (0.8 mL, 12.3 mmol) in ethylene glycol (15 mL) was stirred at ambient temperature for 30 min and then slowly heated to 150° C. and maintained for 2 h. The reaction mixture was allowed to cool to ambient temperature, poured into ice-water and extracted with diethyl ether. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude compound. Purification by column chromatography over silica gel (60-120 mesh) using petroleum ether as eluent to afford 2-methyl-1-phenyl-pyrrole (430 mg, 66%) as a yellow oil.

Aufarbeitung

  1. temperatureslowly heated to 150° C.
  2. temperaturemaintained for 2 h
  3. temperatureto cool to ambient temperature
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude compound
  10. customPurification by column chromatography over silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-9e7277e56ab44dc1aff4ee6223583bf7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993574B2

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