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m-Chloroperbenzoic acid → 4-[5-(3,5-Dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester

HRID 69401
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HRID 69401 반응식
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14](SC)[C:13]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:12][N:11]=2)=[CH:6][C:5]=1[CH3:29].Cl[C:32]1C=C(C=CC=1)C(OO)=O.[S:42](S([O-])=O)([O-:45])(=O)=[O:43].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]([S:42]([CH3:32])(=[O:45])=[O:43])[C:13]([C:21]3[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=3)([C:17]([F:20])([F:19])[F:18])[O:12][N:11]=2)=[CH:6][C:5]=1[CH3:29]
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참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acid3회HCID 656671Sodium PyrosulfiteHCID 66986689HCID 66986689, 화합물

생성물 1

HCID 672171444-[5-(3,5-Dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4-methylsulfanyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester (428 mg) in dichloromethane (15 ml) was added 3-chloroperoxybenzoic acid (“MCPBA”) (500 mg) dropwise at ambient temperature. The reaction mixture was stirred for 5 hours then more 3-chloroperoxubenzoic acid (“MCPBA”) (300 mg) was added dropwise. The reaction mixture was allowed to stand at ambient temperature for 3 days. Then more 3-chloroperbenzoic acid (“MCPBA”) (100 mg) was added dropwise. The reaction mixture was allowed to stand at ambient temperature for another day. The reaction mixture was then treated with aqueous sodium metabisulfite (saturated) and extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: heptane/diethyl ether 6:4) to give 4-[5-(3,5-dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester (300 mg) as white foam. 1H-NMR (CDCl3, 400 MHz): 8.01-7.52 (m, 6H), 5.28 (s, 1H), 3.91 (s, 3H), 2.65 (s, 3H), 2.47 (s, 3H) ppm.

후처리

  1. waitto stand at ambient temperature for 3 days
  2. waitto stand at ambient temperature for another day
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (eluent: heptane/diethyl ether 6:4)

출처 및 근거

ORD 기록
ord-cb4b6812d6c84ab2a9455ed7c0a09d7b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822502B2

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