Dimethylformamide → 2,5-Dimethylthiophene-3-carbaldehyde

HRID 357768

반응식

HRID 357768 반응식
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH3:11][C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1>O>[CH3:11][C:12]1[S:13][C:14]([CH3:17])=[CH:15][C:16]=1[CH:8]=[O:9]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 125142,5-DimethylthiopheneHCID 24813Phosphorus oxychloride

생성물 1

HCID 27627592,5-Dimethylthiophene-3-carbaldehyde수율 10.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

Phosphorus oxychloride (10 ml) was slowly added dropwise to dimethylformamide (30 g) under ice-cooling, and 2,5-dimethylthiophene (11.2 g) was added. The mixture was stirred at 100° C. for 15 hours, poured into water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2,5-dimethyl-3-thiophenecarbaldehyde (1.41 g). 2,5-Dimethyl-3-thiophenecarbaldehyde (3.89 g) synthesized in this manner was dissolved in acetonitrile (30 ml), and sodium dihydrogen phosphate (1.2 g) in water (15 ml) and 30% aqueous hydrogen peroxide (3.5 ml) were added dropwise. The mixture was stirred at room temperature for 2 hours, alkalified with 1N aqueous sodium hydroxide and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2,5-dimethyl-3-thiophenecarboxylic acid (4.09 g) as crystals.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5f2562df807c47ee9af68f2b2cff287a
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840917

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