Acetic Acid → 1-(2-Methylthiazol-4-yl)-3-phenylpropan-1,3-dione

HRID 1061548

反応式

HRID 1061548 の反応式
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH3:12][C:13]1[S:14][CH:15]=[C:16]([C:18](OCC)=[O:19])[N:17]=1.C(O)(=O)C>C1COCC1.O>[CH3:12][C:13]1[S:14][CH:15]=[C:16]([C:18](=[O:19])[CH2:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])[N:17]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

生成物 1

HCID 222852021-(2-Methylthiazol-4-yl)-3-phenylpropan-1,3-dione収率 88.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a boiling suspension of sodium hydride (60% in oil) (360 mg) in anhydrous THF (10 ml) was added dropwise a solution of acetophenone (720 mg) and ethyl 2-methylthiazol-4-carboxylate (1.20 g) in anhydrous THF (10 ml), followed by 10 minutes of heating under refluxing. After the reaction solution was cooled, a mixed solution of acetic acid (1 ml) and water (30 ml) was added thereto, and the resulting mixture was extracted with ethyl acetate. The extracted solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v)) to obtain 1-(2-methylthiazol-4-yl)-3-phenylpropan-1,3-dione (1.3 g, 88%) as yellow crystals. Hereinafter, the compounds of Reference Examples 2 to 10 were obtained similarly.

後処理

  1. temperatureof heating
  2. temperatureunder refluxing
  3. temperatureAfter the reaction solution was cooled
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extracted solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v))

出典と根拠

ORDレコード
ord-1e638a89455e43068ab34f0660e04f22
出典データセット
uspto-grants-2005_11
特許番号
US06960591B2

関連ノート

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