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

HRID 860683

Reaktionsgleichung

Reaktionsgleichung von HRID 860683
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178506616HCID 178506616, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%

Quellen und Nachweise

ORD-Eintrag
ord-bab5aa22367e45bea9b2e2480dc93bae
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153878B2

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