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N,N'-Dimethylethylenediamine → 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone

HRID 12553
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12553
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19]([O:21]CC)=O)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24]NCCNC.C[Al](C)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](=[O:21])[CH3:24])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8070N,N'-DimethylethylenediamineHCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2×HCID 16682925Trimethylaluminum

Produkt 1

HCID 593388261-(5,6-Diphenyl-pyridin-2-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
112 °C

Versuchsvorschrift

General Procedure O. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 246 mg, 0.81 mmol) in toluene (5 ml) was added N,N′-dimethylethylenediamine (DMEDA, 78.7 mg, 0.89 mmol) and trimethylaluminum (1.2 ml, 2.44 mmol, 2 M in toluene) dropwise under argon at room temperature. After the mixture was refluxed at 112° C. for 2.5 hours, it was quenched with water, and the products were extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as a yellow solid.

Aufarbeitung

  1. customit was quenched with water
  2. extractionthe products were extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solvents were concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a2896fc6ab234e46af24b98823239a8b
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728014B2

Notizen zur Reaktion

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