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

HRID 34732

Reaction equation

HRID 34732 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 249986Oxo(thiophen-3-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-e0bc3c474aa34752b1b82f750db34eec
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Linked notes

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