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Formaldehyde → HCID 17842393, Verbindung

HRID 459454
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459454
C=O.[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15](/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][CH:17]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:26](OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]2[N:14]=[C:15](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:16][C:17]=2[CH2:26]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22710974HCID 22710974, Verbindung

Produkt 1

HCID 17842393HCID 17842393, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acid
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Paraformaldehyde (54.5 mg) and p-toluenesulfonic acid (7.2 mg) were added to a solution of 4-[2-(tert-butoxycarbonylamino)ethyl]-2-(trans-styryl)oxazole (190 mg) in toluene (15 ml) at room temperature. After heating under reflux for 1 hour, the reaction mixture was allowed to cool, and ethyl acetate (15 ml) and a saturated aqueous solution (15 ml) of sodium hydrogen-carbonate were added to the reaction mixture to separate an organic layer. After the water layer was extracted with ethyl acetate (10 ml), the resultant organic layers were combined and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→2:1) to obtain the title compound (153 mg) as a colorless oil.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool
  4. customto separate an organic layer
  5. extractionAfter the water layer was extracted with ethyl acetate (10 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1→2:1)

Quellen und Nachweise

ORD-Eintrag
ord-72c33b9999494948ab0a10124b4a970c
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07192968B2

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