Dimethylformamide → 5-Hexylthiophene-2-carboxaldehyde

HRID 425248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425248
C([Li])CCC.[CH2:6]1[CH2:10][O:9][CH2:8][CH2:7]1.[CH2:11]([C:17]1[S:18]C=CC=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CN(C=O)C>[Cl-].[NH4+]>[CH2:11]([C:17]1[S:18][C:6]([CH:10]=[O:9])=[CH:7][CH:8]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 877932-HexylthiopheneHCID 178418339Butyllithium

Produkt 1

HCID 114696515-Hexylthiophene-2-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere at 0° C., 24 ml of n-butyllithium (1.6M in hexane) were added by dripping to a THF solution containing 2-hexylthiophene (5 g). The solution was then stirred for another 15 minutes and, after adding DMF (5 ml), set to room temperature. The resulting solution was then poured into a IN ammonium chloride solution and extracted with methylene chloride. An organic layer was washed with water and dried with anhydrous magnesium sulfate. A crude product was collected by removing the solvent and then purified by a column chromatograph (carrier: silicon dioxide; eluate: hexane/methylene chloride-4/1 (volume ratio)) to obtain 4.6 g of a product.

Aufarbeitung

  1. customset to room temperature
  2. extractionextracted with methylene chloride
  3. washAn organic layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customA crude product was collected
  6. customby removing the solvent
  7. custompurified by a column chromatograph (carrier: silicon dioxide; eluate: hexane/methylene chloride-4/1 (volume ratio))

Quellen und Nachweise

ORD-Eintrag
ord-f9a17fe1eb6143a68959b58f958d2121
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106198B2

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