Dimethylformamide → 2,5-Dimethylthiophene-3-carbaldehyde

HRID 357768

反応式

HRID 357768 の反応式
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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 125142,5-DimethylthiopheneHCID 24813Phosphorus oxychloride

生成物 1

HCID 27627592,5-Dimethylthiophene-3-carbaldehyde収率 10.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f2562df807c47ee9af68f2b2cff287a
出典データセット
uspto-grants-1998_11
特許番号
US05840917

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