3-Methylbenzoyl chloride → N-benzyl-2-(3'-methylbenzoyl)pyrrole

HRID 1721563

Reaktionsgleichung

Reaktionsgleichung von HRID 1721563
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH2:11]([N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:11]([N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 743753-Methylbenzoyl chlorideHCID 749221H-Pyrrole, 1-(phenylmethyl)-

Produkt 1

HCID 22413287N-benzyl-2-(3'-methylbenzoyl)pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In a flask were placed 3.0 ml (22.9 mmol) 3-methylbenzoyl chloride and 50 ml methylene chloride. Then 22.9 ml (1.0M in CH2Cl2, 22.9 mmol) stannic chloride was added dropwise. The contents of the flask were mixed for 5 minutes, then 3.6 g (22.9 mmol) N-benzylpyrrole in 10 ml methylene chloride was added dropwise. The reaction mixture was stirred overnight, then quenched with water, washed with brine, dried and condensed to yield an oil. The oil was purified by flash chromatography with ethyl acetate/hexanes/silica gel, yielding two fractions. These were analyzed spectroscopically; one was found to be the desired 2-benzoyl compound, the other the corresponding 3-benzoyl compound.

Aufarbeitung

  1. customIn a flask were placed
  2. additionThe contents of the flask were mixed for 5 minutes
  3. customquenched with water
  4. washwashed with brine
  5. customdried
  6. customcondensed
  7. customto yield an oil
  8. customThe oil was purified by flash chromatography with ethyl acetate/hexanes/silica gel
  9. customyielding two fractions

Quellen und Nachweise

ORD-Eintrag
ord-d6200c2997354d529dd7212cc1a18ade
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05512537

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