Water → 2-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione

HRID 1916024노트

반응식

HRID 1916024 반응식
[Na].S(NN=[CH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)(C1C=CC(C)=CC=1)(=O)=O.[CH:22]([N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])=[CH2:23].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH:14]2[CH2:23][CH:22]2[N:24]2[C:25](=[O:34])[C:26]3[C:27](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:29])=[CH:20][CH:19]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 866384034-Chlorobenzaldehyde tosyl hydrazone sodium salt

생성물 1

HCID 684102072-[2-(4-Chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione수율 26.3%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 168478Rhodium acetate촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-chlorobenzaldehyde tosyl hydrazone sodium salt (1.67 g, 5.05 mmol), benzyltriethylammoniumchloride (115 mg, 0.5 mmol), rhodium acetate (20 mg, 0.05 mmol) and N-vinylphtalimide (4.32 g, 25.0 mmol) in dry 1,4-dioxane (13 ml) was stirred for one day under nitrogen at room temperature. Water (35 ml) was added to the mixture and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over Na2SO4. Evaporation gave the crude material, which was purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1). To afford 392 mg (26.3% of theory) of 2-[2-(4-chloro-phenyl)-cyclopropyl]-isoindole-1,3-dione in the form of a solid.

후처리

  1. extractionthe aqueous phase was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customEvaporation
  4. customgave the crude material, which
  5. customwas purified by flash chromatography over silicagel (eluent: hexane/ethylacetate 1:1)

출처 및 근거

ORD 기록
ord-ff56d522faa54c379f2ff6866cf26c3e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618023B2

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