Acetic Acid → 2,5-Dimethyl-1-phenylpyrrole

HRID 641808

Reaktionsgleichung

Reaktionsgleichung von HRID 641808
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9](=O)[CH2:10][CH2:11][C:12](=O)[CH3:13].CC(O)=O>Cl>[CH3:13][C:12]1[N:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]([CH3:8])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6115AnilineHCID 80352,5-Hexanedione

Produkt 1

HCID 665182,5-Dimethyl-1-phenylpyrroleAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A 25 mL round-bottom flask was charged with aniline (1 mL, 8.77 mmol), hexane-2,5-dione (4 mL, 43.86 mmol) and AcOH (5 mL). The reaction mixture was refluxed for 4 hrs. The mixture was diluted with HCl (10%) and extracted with EtOAc. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure to give 190 mg of compound 4 (75%). MS [M++1]=172, LC-MS: tR=2.54 min.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 hrs
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-efd34f39eea241b58726aa926f4bc18c
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696227B2

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