Dimethylformamide → 5-Hexylthiophene-2-carboxaldehyde

HRID 425248Notes

Reaction equation

HRID 425248 reaction equation
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]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 877932-HexylthiopheneHCID 178418339Butyllithium

Product 1

HCID 114696515-Hexylthiophene-2-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-f9a17fe1eb6143a68959b58f958d2121
Source dataset
uspto-grants-2012_01
Patent number
US08106198B2

Reaction notes

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