1,2-Dichloroethane → (3-{1-Methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethylsulfanyl}-phenyl)-acetic Acid Methyl Ester

HRID 860683

反応式

HRID 860683 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[O:5][C:6]=1[C:7](O)([CH3:9])[CH3:8].[CH3:21][O:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([SH:31])[CH:26]=1.ClCCCl>C(OCC)(=O)C.[I-].[Zn+]>[CH3:21][O:22][C:23](=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([S:31][C:7]([CH3:9])([C:6]2[O:5][C:4]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[N:3][C:2]=2[CH3:1])[CH3:8])[CH:26]=1

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 14820216Methyl 2-(3-mercaptophenyl)acetateHCID 695893092-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol

生成物 1

HCID 69589602(3-{1-Methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethylsulfanyl}-phenyl)-acetic Acid Methyl Ester

試薬・触媒・溶媒 2

HCID 178506616HCID 178506616、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol (0.1 g, 0.351 mmol), (3-Mercapto-phenyl)-acetic acid methyl ester (0.070 g, 0.386 mmol), zinc (I) iodide (0.056 g, 0.176 mmol), and 1,2-dichloroethane (2 mL) is stirred at room temperature 24 hr. The reaction mixture is diluted with ethyl acetate (25 mL), and washed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each), dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 8:2 hexanes:ethyl acetate to afford the product as a colorless film, 0.105 g, 66%. MS M++1 286. The structure is confirmed by 1H NMR spectroscopy.

後処理

  1. washwashed with aqueous saturated sodium hydrogen carbonate, water, brine (25 mL each)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified via silica chromatography
  6. washeluting with 8:2 hexanes
  7. customethyl acetate to afford the product as a colorless film, 0.105 g, 66%

出典と根拠

ORDレコード
ord-bab5aa22367e45bea9b2e2480dc93bae
出典データセット
uspto-grants-2006_12
特許番号
US07153878B2

関連ノート

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