Hydrochloric Acid → 2-(2-Fluorobenzoyl)-3-thiophenecarboxaldehyde

HRID 483792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483792
C[O:2][CH:3](OC)[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16].C(O)C.Cl>O.CCOCC>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([C:5]1[S:6][CH:7]=[CH:8][C:4]=1[CH:3]=[O:2])=[O:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15728739HCID 15728739, Verbindung

Produkt 1

HCID 128984342-(2-Fluorobenzoyl)-3-thiophenecarboxaldehydeAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 2-(2-fluorobenzoyl)-3-thiophenecarboxaldehyde dimethylacetal was added a solution of absolute ethanol (575 ml) and hydrogen chloride (39 g). The reaction mixture was heated at reflux for 10 mins, with stirring under nitrogen. The solution was cooled to room temperature, diluted with water and ether, and the layers were separated. The aqueous layer was extracted with ether, and the combined organic layers washed with dilute aqueous sodium bicarbonate solution, brine, dried over anhydrous potassium carbonate, filtered and concentrated. The residue was purified by flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes) to afford 20.3 g (27%) of product.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 10 mins
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ether
  5. washthe combined organic layers washed with dilute aqueous sodium bicarbonate solution, brine
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel, 0-20% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8c3522d0e0934f48a94688a4f4b11e71
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05227388

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