Ammonium Chloride → (2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone

HRID 1986428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986428
[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[NH2:1][C:2]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])=[CH:10][C:3]=1[C:4]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 866056272-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamideHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 68832602(2-Amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanoneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbenzamide (5.0 g, 16 mmol) in tetrahydrofuran (100 ml) was added dropwise 2.0 M solution (20 ml) of phenylmagnesium bromide in tetrahydrofuran at −78° C. The temperature of the reaction mixture was raised, and the mixture was stirred at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column to give (2-amino-5-{[tert-butyl(dimethyl)silyl]oxy}-phenyl)(phenyl)methanone (3.4 g, yield 65%) as a yellow oil.

Aufarbeitung

  1. temperatureThe temperature of the reaction mixture was raised
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-bf0e8f6b58e9471fbf797d5ee831fcce
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547710B2

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