Carbon Tetrachloride → 2-[2-({[4-(Trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acid

HRID 1795124ノート

反応式

HRID 1795124 の反応式
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[CH2:22][OH:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.I([O-])(=O)(=O)=[O:35].[Na+]>O.[Ru](Cl)(Cl)Cl.O>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[C:22]([OH:35])=[O:23])(=[O:10])=[O:11])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 221855162-[2-(Hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)benzenesulfonateHCID 23667635Sodium periodate

生成物 1

HCID 221856342-[2-({[4-(Trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acid収率 95%

試薬・触媒・溶媒 2

HCID 6093376Ruthenium trichloride hydrate触媒HCID 962Water溶媒

実験手順

A mixture of 2-[2-(hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)-benzenesulfonate (0.70 g, 1.9 mmol), carbon tetrachloride (2.5 mL), acetonitrile (2.5 mL), water (3.8 mL), sodium periodate (1.8 g, 8.4 mmol) and ruthenium choride hydrate (75 mg, 0.4 mmol) is stirred at room temperature overnight. The reaction is partitioned between ethyl acetate and dilute HCl. The organic layer is filtered through anhydrous sodium sulfate, evaporated and purified on silica gel in ethyl acetate-methylene chloride-acetic acid mixtures. The product, 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acid, is obtained as a mixture of isomers. A yield of 95% is obtained.

後処理

  1. customThe reaction is partitioned between ethyl acetate and dilute HCl
  2. filtrationThe organic layer is filtered through anhydrous sodium sulfate
  3. customevaporated
  4. custompurified on silica gel in ethyl acetate-methylene chloride-acetic acid mixtures

出典と根拠

ORDレコード
ord-7b7a4e4992db4792893a49633a7aa668
出典データセット
uspto-grants-2006_04
特許番号
US07026339B2

反応ノート

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