1-(Thiophen-3-yl)ethanone → Oxo(thiophen-3-yl)acetaldehyde

HRID 34732

Reaktionsgleichung

Reaktionsgleichung von HRID 34732
[C:1]([C:4]1[CH:8]=[CH:7][S:6][CH:5]=1)(=[O:3])[CH3:2].[O:9]1CCOCC1>O>[S:6]1[CH:7]=[CH:8][C:4]([C:1]([CH:2]=[O:9])=[O:3])=[CH:5]1

Komponenten

4

Edukt 2

HCID 151161-(Thiophen-3-yl)ethanoneHCID 312751,4-Dioxane

Produkt 1

HCID 249986Oxo(thiophen-3-yl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

3-Acetylthiophene (20.0 g., 0.159 mol) and SeO2 (19.4 g., 0.175 mol) were dissolved 100 ml. dioxane and 8 ml. H2O by warming to 35°, then heated at reflux 16 hours. The reaction mixture was cooled, filtered and the filtrate stripped to a sludge (the hydrate of title product in crude form). The latter was distilled at reduced pressure to yield title product contaminated with about 10% starting material, 8.53 g.; tlc (5:3 hexane:ethyl acetate) Rf 0.27 (title product) and 0.59 (3-acetylthiophene). The latter was chromatographed on silica gel with 5:3 hexane:ethyl acetate is eluant. Clean product fractions were combined stripped to a solid, triturated with hexane, filtered and the solids (5.60 g.) sublimed to yield purified title product, 3.20 g.; tlc Rf 0.27 as above; sublimation point 70°/1 mm; ms: parent 141, base 111.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. distillationThe latter was distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e0bc3c474aa34752b1b82f750db34eec
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762921

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