Ethylene Glycol → HCID 59660700, Verbindung

HRID 1641430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1641430
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH3:14])=[C:12]([CH:15]=[O:16])[CH:11]=[N:10]2)=[CH:5][CH:4]=1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:12]1[CH:11]=[N:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:13]=1[CH3:14]

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 27797351-(4-Methoxyphenyl)-5-methyl-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 59660700HCID 59660700, VerbindungAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-methoxy-phenyl)-5-methyl-1H-pyrazole-4-carbaldehyde (0.5 g, 2.3 mmol), ethylene glycol (1.44 g, 23.1 mmol) and p-toluenesulfonic acid (0.2 g, 1.2 mmol) in toluene (10 mL) was refluxed for 18 h (Dean Stock to remove water formed). After it was allowed to cool to room temperature, the reaction mixture was diluted with ethyl acetate, washed with sat. NaHCO3 (aq) and brine, and dried over Na2SO4. After concentrated, the residue was purified by a column chromatography on silica gel to yield the title compound (0.35 g, 58%); MS (APCI) m/z: 261 (M+1, 80).

Aufarbeitung

  1. temperaturewas refluxed for 18 h
  2. custom(Dean Stock to remove water formed)
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washwashed with sat. NaHCO3 (aq) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated
  7. customthe residue was purified by a column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a6db0c52a4614a47882bc7d6906dede7
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08115005B2

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