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Acetic Acid → HCID 22013889, Verbindung

HRID 1532747
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1532747
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.[C:24]([O:33][CH:34]([CH3:36])[CH3:35])(=[O:32])[CH2:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[C:25]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[C:24]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])=[CH:18][CH:17]=1
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Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 83223Diisopropyl malonateHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Produkt 1

HCID 22013889HCID 22013889, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (3.07 g, 10 mmol) synthesized according to the method described in WO95/18125 in toluene (40 ml) were added diisopropyl malonate (1.88 g, 10 mmol), acetic acid (300 mg) and piperidine (425 mg). While removing water through Dean-Stark trap, the mixture was refluxed under heating. Eight hours later, toluene was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=75:25) and the fraction containing the objective substance was concentrated under reduced pressure to give the title compound (4.2 g, yield 88%) as a yellow oil.

Aufarbeitung

  1. customWhile removing water through Dean-Stark trap
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating
  4. customEight hours later, toluene was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent; hexane:ethyl acetate=75:25)
  6. additionthe fraction containing the objective substance
  7. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ecfa2bd806f941b0acffa5230ebdfe50
Quelldatensatz
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06204277B1

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