3,4-dihydro-2H-pyran → Dipyranyl ethylmalonate

HRID 1450648

반응식

HRID 1450648 반응식
[CH2:1]([CH:3]([C:7]([OH:9])=[O:8])[C:4]([OH:6])=[O:5])[CH3:2].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.[H-].[Na+].[C:18]1([C:24]2[CH:28]=[C:27](C(Cl)=O)[O:26]N=2)[CH:23]=CC=CC=1>O1CCCC1.O.C(O)(=O)C.C1C=CC=CC=1>[CH2:1]([CH:3]([C:7]([O:9][CH:27]1[CH:28]=[CH:24][CH:18]=[CH:23][O:26]1)=[O:8])[C:4]([O:6][CH:15]1[CH:14]=[CH:13][CH:12]=[CH:11][O:10]1)=[O:5])[CH3:2]

참가 물질

9

반응물 4

HCID 80803,4-dihydro-2H-pyranHCID 11756Ethylmalonic acidHCID 24758Sodium hydrideHCID 143973243-Phenylisoxazole-5-carbonyl chloride

생성물 1

HCID 19976934Dipyranyl ethylmalonate

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To 130 ml of benzene, were added 12.9 g (97.7 mmol) of ethylmalonic acid, 20.2 g (240.5 mmol) of 3,4-dihydropyran and 2 droplets of concentrated suluric acid. They were reacted for 1 hour under ice cooling, whereby dipyranyl ethylmalonate was prepared. The reaction mixture was added with 4.7 g (117.5 mmol) of 60% sodium hydride, followed by heating under stirring at 50° C. for 5 hours. A solution of 15.0 g (79.4 mmol) of 3-phenylisoxazole-5-carboxylic acid chloride, which had been synthesized above in the procedure (3), in 70 ml of tetrahydrofuran was added under ice cooling to the above-prepared reaction mixture. The mixture thus obtained was then subjected to a reaction at room temperature for 12 hours. The reaction mixture was added with 20 ml of acetic acid and then heated under reflux for 8 hours. The reaction mixture so obtained was poured into water and then extracted with benzene. The organic layer was washed successively with water, an aqueous solution of sodium hydrogen- carbonate and saturated saline, and was then dried over anhydrous sodium sulfate. After the benzene was distilled off, hexane was added into the residue. Crystals precipitated was collected by filtration, so that 3-phenyl-5-butyrylisoxazole was obtained.

후처리

  1. customThey were reacted for 1 hour under ice cooling
  2. temperatureby heating
  3. additionwas added under ice cooling to the above-prepared reaction mixture
  4. customThe mixture thus obtained
  5. customwas then subjected to a reaction at room temperature for 12 hours
  6. temperatureheated
  7. temperatureunder reflux for 8 hours
  8. customThe reaction mixture so obtained
  9. extractionextracted with benzene
  10. washThe organic layer was washed successively with water
  11. dry with materialan aqueous solution of sodium hydrogen- carbonate and saturated saline, and was then dried over anhydrous sodium sulfate
  12. distillationAfter the benzene was distilled off
  13. additionhexane was added into the residue
  14. customCrystals precipitated
  15. filtrationwas collected by filtration, so that 3-phenyl-5-butyrylisoxazole
  16. customwas obtained

출처 및 근거

ORD 기록
ord-23d2352e0cff437194d245e2d6153e3a
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602160

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