Mesitylene → 5-mesityl-1H-pyrrole-3-carbaldehyde

HRID 1012486

Reaktionsgleichung

Reaktionsgleichung von HRID 1012486
Br[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1(C)C=C(C)C=C(C)C=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:10]1([CH3:9])[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[C:2]1[NH:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

Komponenten

8

Edukt 5

HCID 7947MesityleneHCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 578319835-bromo-1H-pyrrole-3-carbaldehyde

Produkt 1

HCID 866309875-mesityl-1H-pyrrole-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-1H-pyrrole-3-carbaldehyde (0.87 g), 2,4,6-trimethylphenylboronic acid (3.28 g), cesium carbonate (13.0 g), tri-tert-butylphosphine (0.10 g), tris(dibenzylideneacetone)dipalladium (0) (0.23 g) and mesitylene (200 mL) was stirred with heating under reflux for 5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1) to give the title compound as a brown amorphous form (yield 0.30 g, 28%).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 5 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9f4f196355aa4aaa898ca2ea679e70bb
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977488B2

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