Dimethylformamide → 5-Octylthiophene-2-carbaldehyde

HRID 2057645Notes

Reaction equation

HRID 2057645 reaction equation
[CH2:1]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].P(Cl)(Cl)(Cl)=O.CN(C)[CH:21]=[O:22]>>[CH2:1]([C:9]1[S:10][C:11]([CH:21]=[O:22])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 701532-n-Octylthiophene

Product 1

HCID 137915885-Octylthiophene-2-carbaldehyde

Procedure

To a stirred solution of 80.1 g. of 2-octylthiophene in 70 ml. dimethylformamide is added dropwise 42.4 ml. of phosphorus oxychloride. After addition, the solution is made warmed at 100° for 1 hour, then poured into 600 ml. ice. After neutralization with sodium acetate, the resulting oil is extracted with ether. The ether is washed with water and aqueous potassium carbonate, dried, and distilled in vacuo to give the title compound as an oil.

Workup

  1. additionAfter addition
  2. temperaturethe solution is made warmed at 100° for 1 hour
  3. additionpoured into 600 ml
  4. extractionAfter neutralization with sodium acetate, the resulting oil is extracted with ether
  5. washThe ether is washed with water and aqueous potassium carbonate
  6. customdried
  7. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-ea51ddfd615a4cac95c6cd81a4bc64f2
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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