Water → 2,5-Dimethyl-3-thienyl cyclopropyl ketone

HRID 1589731

Reaktionsgleichung

Reaktionsgleichung von HRID 1589731
[CH3:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[CH:8]1([C:11](Cl)=[O:12])[CH2:10][CH2:9]1.[Sn](Cl)(Cl)(Cl)Cl.O>ClCCl>[CH:8]1([C:11]([C:6]2[CH:5]=[C:4]([CH3:7])[S:3][C:2]=2[CH3:1])=[O:12])[CH2:10][CH2:9]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 125142,5-DimethylthiopheneHCID 24287Tin tetrachlorideHCID 77637Cyclopropanecarbonyl chloride

Produkt 1

HCID 431614402,5-Dimethyl-3-thienyl cyclopropyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2,5 Dimethylthiophene (50 g, 0.446 mole) and cyclopropylcarbonyl chloride (54.36 g, 0.52 mole) were dissolved in dichloromethane (500 ml) and cooled in an ice bath. Tin(IV) chloride (122.44 g, 0.470 mole) in dichloromethane (150 ml) was added slowly over 1 hour with stirring to form a deep red solution. The mixture was warmed to room temperature and stirred for a further hour. The mixture was then poured into cold water (750 ml) and stirred rapidly for 30 min. The dichloromethane layer was washed with cold water and dried over magnesium sulfate. The dichloromethane solvent was removed to give the ketone, 2,5-dimethyl-3-thienyl cyclopropyl ketone, as a brown oil (73.25 g).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customto form a deep red solution
  3. stirringstirred for a further hour
  4. stirringstirred rapidly for 30 min
  5. washThe dichloromethane layer was washed with cold water
  6. dry with materialdried over magnesium sulfate
  7. customThe dichloromethane solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-bb1f784aa37c4fd08eacb4796784605e
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200116

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