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

HRID 1916024ノート

反応式

HRID 1916024 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 168478Rhodium acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff56d522faa54c379f2ff6866cf26c3e
出典データセット
uspto-grants-2013_12
特許番号
US08618023B2

反応ノート

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