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

HRID 2099846

반응식

HRID 2099846 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-c203852ddbd149b285cb60be463c060b
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569688B2

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