Dimethylformamide → 5-Phenylthiophene-2-carbaldehyde

HRID 1761376Notes

Reaction equation

HRID 1761376 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].CN(C)[CH:21]=[O:22]>>[CH:21]([C:14]1[S:13][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:16][CH:15]=1)=[O:22]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 699992-Phenylthiophene

Product 1

HCID 1770535-Phenylthiophene-2-carbaldehyde

Procedure

Under a nitrogen atmosphere 35 mL of dimethylformamide was cooled to 0° C. and 7 mL of phosphorus oxychloride was added with stirring. The solution was allowed to warm to ambient temperature, and then a solution of 10.0 grams (0.0625 mole) of 2-phenylthiophene in 10 mL of dimethylformamide was added in one portion. The reaction mixture was heated to 80° C. where it stirred for 24 hours and then poured into 250 mL of an aqueous 10% sodium hydroxide solution containing 50 grams of ice. The resulting slurry was extracted with diethyl ether, and the extract was washed in succession with water, an aqueous solution saturated with sodium chloride, and water. The organic layer was concentrated under reduced pressure to a solid residue which was dried under high vacuum to yield 6.8 grams of 5-formyl-2-phenylthiophene.

Workup

  1. temperatureThe reaction mixture was heated to 80° C. where it
  2. stirringstirred for 24 hours
  3. extractionThe resulting slurry was extracted with diethyl ether
  4. washthe extract was washed in succession with water
  5. concentrationThe organic layer was concentrated under reduced pressure to a solid residue which
  6. customwas dried under high vacuum

Sources & evidence

ORD record
ord-d96c780540f6498b84508dd3cb570f5a
Source dataset
uspto-grants-1989_05
Patent number
US04826829

Reaction notes

Loading…