Ethyl Acetate → {2-(3-Hydroxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

HRID 1698638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698638
[CH3:1][O:2][C:3](=[O:41])[N:4]=[C:5]([S:39][CH3:40])[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][Si](C(C)C)(C(C)C)C(C)C)[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[CH3:1][O:2][C:3](=[O:41])[N:4]=[C:5]([S:39][CH3:40])[C:6]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([OH:28])[CH:21]=1)=[N:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([CH3:19])[O:16][N:15]=2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 72312841{2-(4-Methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester

Produkt 1

HCID 72312763{2-(3-Hydroxy-4-methoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl esterAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 2724141Tetrabutylammonium FluorideLösungsmittel

Versuchsvorschrift

After dissolving 3.52 g of {2-(4-methoxy-3-triisopropylsilanyloxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylimino]-1-methylsulfanylethylidene}carbamic acid methyl ester in 50 ml of THF, 6.49 ml of TBAF (1.0 M, THF solution) was added and the mixture was stirred at room temperature for 15 hours. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.88 g, isomeric mixture) as a light yellow solid.

Aufarbeitung

  1. additionwas added
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-007f6be6e5d6422881f611bdfd2b8570
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163787B2

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