Water → Ethyl 2-(2,1-benzisothiazol-4-yl)cyclopropanecarboxylate

HRID 1639852ノート

反応式

HRID 1639852 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[N:9]1[S:10][CH:11]=[C:12]2[C:17](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=[CH:14][C:13]=12.O>CS(C)=O>[N:9]1[S:10][CH:11]=[C:12]2[C:17]([CH:18]3[CH2:4][CH:19]3[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=[CH:14][C:13]=12

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720661ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylate

生成物 1

HCID 59334632Ethyl 2-(2,1-benzisothiazol-4-yl)cyclopropanecarboxylate収率 53%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

実験手順

Under nitrogen atmosphere, to a suspension of sodium hydride (60%, 1.08 g, 24.7 mmol) in dimethyl sulfoxide (100 mL) was added a solution of trimethylsulfoxonium iodide (5.43 g, 24.7 mmol) in dimethyl sulfoxide (100 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl(2E)-3-(2,1-benzisothiazol-4-yl)acrylate (4.80 g, 20.6 mmol) in dimethyl sulfoxide (200 mL) at 0° C., and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (2.70 g, yield 53%).

後処理

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

出典と根拠

ORDレコード
ord-32cb54ed615947d68a27ef76e4da116a
出典データセット
uspto-grants-2012_02
特許番号
US08110585B2

反応ノート

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