Sulfuric Acid → 3-(4-Methylphenyl)-5-butyrylisoxazole

HRID 1742534

반응식

HRID 1742534 반응식
[H-].[Na+].C(C(C(OC1C=CC=CO1)=O)C(OC1C=CC=CO1)=O)C.[CH2:24]([CH:26]([C:30]([OH:32])=O)C(O)=O)[CH3:25].O1C=CCCC1.S(=O)(=O)(O)O.C(C(C([O-])=O)C([O-])=O)C.C(OC1C=CC=CO1)(=O)CC(OC1C=CC=CO1)=O.[Na].[CH3:73][C:74]1[CH:79]=[CH:78][C:77]([C:80]2[CH:84]=[C:83](C(Cl)=O)[O:82][N:81]=2)=[CH:76][CH:75]=1>C1C=CC=CC=1.O.C(O)(=O)C.O1CCCC1>[CH3:73][C:74]1[CH:75]=[CH:76][C:77]([C:80]2[CH:84]=[C:83]([C:30](=[O:32])[CH2:26][CH2:24][CH3:25])[O:82][N:81]=2)=[CH:78][CH:79]=1

참가 물질

13

반응물 8

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 11756Ethylmalonic acidHCID 24758Sodium hydrideHCID 6950106EthylpropanedioateHCID 19976934Dipyranyl ethylmalonateHCID 537159153-(4-Methylphenyl)isoxazole-5-carboxylic acid chlorideHCID 67715643Sodium dipyranyl malonate

생성물 1

HCID 199769533-(4-Methylphenyl)-5-butyrylisoxazole

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In 50 ml of benzene, 2.6 g (57.5 mmol) of 60% sodium hydride were added to dipyranyl ethylmalonate which had been prepared from 5.7 g (43.2 mmol) of ethylmalonic acid, 9.0 g (107.1 mmol) of 3,4-dihydropyran and 1 droplet of concentrated sulfuric acid. At 40°-50° C., the ethylmalonate was converted to sodium dipyranyl malonate, to which a tetrahydrofuran solution of 3-(4-methylphenyl)isoxazole-5-carboxylic acid chloride synthesized above in the procedure (3) was added dropwise at room temperature. They were reacted for 3 hours. The reaction mixture was added with 10 ml of acetic acid and then heated under reflux for 6 hours. The mixture thus obtained was added into water and then extracted with benzene. The benzene extract was washed successively with an aqueous solution of sodium hydrogencarbonate and water. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. Hexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole precipitated as crystals was collected by filtration. Analytical results of the crystals obtained: Yield: 6.3 g (76.5%). Melting point: 86°-87° C.

후처리

  1. customAt 40°-50° C.
  2. customsynthesized above in the procedure (3)
  3. additionwas added dropwise at room temperature
  4. customThey were reacted for 3 hours
  5. temperatureheated
  6. temperatureunder reflux for 6 hours
  7. customThe mixture thus obtained
  8. extractionextracted with benzene
  9. extractionThe benzene extract
  10. washwas washed successively with an aqueous solution of sodium hydrogencarbonate and water
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off
  13. additionHexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole
  14. customprecipitated as crystals
  15. filtrationwas collected by filtration
  16. customAnalytical results of the crystals
  17. customobtained

출처 및 근거

ORD 기록
ord-601bca7dee614356acfc12d3f0ec5525
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05338857

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