Dimethylformamide → 5-Phenylthiophene-2-carbaldehyde

HRID 414578

反応式

HRID 414578 の反応式
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]

参加物

5

反応物 4

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

生成物 1

HCID 1770535-Phenylthiophene-2-carbaldehyde

実験手順

Under a nitrogen atmosphere 75 mL of dimethylformamide was cooled to 0° C., and 15 mL of phosphorus oxychloride was added with stirring. The solution was allowed to warm to room temperature, and then a solution of 20.4 grams (0.127 mole) of 2-phenylthiophene in 20 mL of dimethylformamide was added in one portion. The reaction mixture was heated to 80° C. where it stirred for 24 hours. It was then poured into 250 mL of an aqueous, 10% sodium hydroxide solution containing 50 grams of ice. The resulting slurry was extracted with chloroform, and the extract was washed in succession with an aqueous solution saturated with sodium chloride and water. The organic phase was dried over anhydrous magnesium sulfate and filtered. TThe filtrate was concentrated under reduced pressure to a brown residue. Purification of this residue by column chromatography on silica gel, eluting with ethyl acetate:n-hexane (15:85) yielded 18.0 grams of 2-formyl-5-phenylthiophene.

後処理

  1. temperatureThe reaction mixture was heated to 80° C. where it
  2. stirringstirred for 24 hours
  3. extractionThe resulting slurry was extracted with chloroform
  4. washthe extract was washed in succession with an aqueous solution saturated with sodium chloride and water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationTThe filtrate was concentrated under reduced pressure to a brown residue
  8. customPurification of this residue by column chromatography on silica gel
  9. washeluting with ethyl acetate:n-hexane (15:85)

出典と根拠

ORDレコード
ord-999ae6327575456f95cc015a3f430191
出典データセット
uspto-grants-1988_12
特許番号
US04792567

関連ノート

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