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

HRID 1061548Notes

Reaction equation

HRID 1061548 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-1e638a89455e43068ab34f0660e04f22
Source dataset
uspto-grants-2005_11
Patent number
US06960591B2

Reaction notes

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