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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
ノート
印刷プレビュー

反応式

HRID 69401 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acid3 回HCID 656671Sodium PyrosulfiteHCID 66986689HCID 66986689、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cb4b6812d6c84ab2a9455ed7c0a09d7b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822502B2

反応ノート

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