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

HRID 1795124노트

반응식

HRID 1795124 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6093376Ruthenium trichloride hydrate촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b7a4e4992db4792893a49633a7aa668
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026339B2

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