Dimethylformamide → [2,2'-Bithiophene]-5-carboxaldehyde

HRID 1901762Notes

Reaction equation

HRID 1901762 reaction equation
P(Cl)(Cl)(Cl)=O.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.[OH-].[Na+].CN(C)[CH:20]=[O:21]>>[CH:20]([C:10]1[S:6][C:7]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)=[O:21]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 681202,2'-Bithiophene

Product 1

HCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

Conditions

Temperature
-10 °C

Procedure

To dimethyl formamide (250 ml) was added phosphoryl chloride (50.2 ml) with quick stirring. 2,2'-Bithiophene (83 g) in dimethyl formamide (200 ml) was then added and stirred at -10° C. for 30 minutes. Then the temperature was raised to 40° C. and was further stirred for 20 hours. The reaction mixture was then poured into crushed ice and stirred for 30 minutes. Sodium hydroxide aqueous solution (10%, 600 ml) was added and the solution was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, concentrated and separated by silica gel chromatography. Product 90 g was obtained, melting point 56°-57° C.

Workup

  1. temperatureThen the temperature was raised to 40° C.
  2. stirringwas further stirred for 20 hours
  3. additionThe reaction mixture was then poured
  4. custominto crushed ice
  5. stirringstirred for 30 minutes
  6. extractionthe solution was extracted with chloroform
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customseparated by silica gel chromatography

Sources & evidence

ORD record
ord-f2af888b5270402797cb77ff3aa42071
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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