Thiophene → 2-(7-Methoxycarbonyl-1-oxoheptyl)thiophene

HRID 2254324

Reaktionsgleichung

Reaktionsgleichung von HRID 2254324
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O.ClCC(OC(=O)CCl)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1>ClC(Cl)C>[CH3:1][O:2][C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:24]1[S:23][CH:27]=[CH:26][CH:25]=1)=[O:12])=[O:13]

Komponenten

5

Edukt 3

HCID 8030ThiopheneHCID 10946Chloroacetic anhydrideHCID 5541918-Methoxy-8-oxooctanoic acid

Produkt 1

HCID 197452382-(7-Methoxycarbonyl-1-oxoheptyl)thiopheneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In 50 ml of dichloroethane were dissolved 9.41 g (0.05 mole) of suberic acid monomethyl ester and 9.83 g (0.0575 mole) of monochloroacetic anhydride. To the resulting solution were added 5.47 g (0.065 mole) of thiophene and 0.71 g of boron trifluoride-diethyl ether complex and the resulting mixture was then stirred at 60° C. for 5 hours. After completion of the reaction, the reaction solution was cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 11.5 g of 2-(7-methoxycarbonyl-1-oxoheptyl)thiophene.

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperaturethe reaction solution was cooled
  3. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c9d73751140432cab76c4d321254801
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05235068

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