Water → trans-Ethyl 2-(2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate

HRID 1639748ノート

反応式

HRID 1639748 の反応式
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][N:10]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11]1.O>CS(C)=O>[CH3:9][N:10]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[C@@H:19]2[CH2:4][C@H:20]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:11]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720667ethyl (2E)-3-(2-methyl-2H-indazol-4-yl)acrylate

生成物 1

HCID 131729433trans-Ethyl 2-(2-methyl-2h-indazol-4-yl)cyclopropanecarboxylate収率 35%

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 (0.650 g, 15.6 mmol) in dimethyl sulfoxide (5.0 mL) was added a solution of trimethylsulfoxonium iodide (3.34 g, 15.6 mmol) in dimethyl sulfoxide (35 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-methyl-2H-indazol-4-yl)acrylate (3.00 g, 13.0 mmol) in dimethyl sulfoxide (30 mL) at 0° C., and the mixture was stirred at room temperature for 12 hr. Water was added, 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=1/1) to give the title compound (1.10 g, yield 35%).

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=1/1)

出典と根拠

ORDレコード
ord-acefa91b1e7145cd89ef4c5b78af4687
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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