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Acetic Acid → (2-Methoxy-5-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester

HRID 1051221
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1051221
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].[CH3:20][Si:21]([CH2:24][Mg]Cl)([CH3:23])[CH3:22].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(O)(=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][C:9]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 45790233Tert-butyl 2-methoxy-5-nitrophenylcarbamateHCID 178418680HCID 178418680, Verbindung

Produkt 1

HCID 90102720(2-Methoxy-5-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl esterAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

A solution of (2-methoxy-5-nitro-phenyl)-carbamic acid tert-butyl ester (1.80 g, 6.71 mmol) in THF (50 mL) was added ((trimethylsilyl)methyl)magnesium chloride (2.47 g, 16.8 mmol) at −70° C. under nitrogen gas. The solution was then stirred at −70° C. for one hour. A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.05 g, 13.4 mmol) in THF (30 mL) was added, the reaction was warmed to 0° C. The reaction was allowed to stir at 0° C. for another hour. The reaction mixture is poured into an aqueous solution of acetic acid (50 mL, 5%). The aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave brown oil. Flash chromatography (80/20 hexanes/ethyl acetate) afforded (2-methoxy-5-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester (1.50 g, 63%) as a light oil.

Aufarbeitung

  1. temperaturethe reaction was warmed to 0° C
  2. stirringto stir at 0° C. for another hour
  3. extractionThe aqueous phase was extracted three times with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration
  7. concentrationfollowed by concentration in vacuo
  8. customgave brown oil

Quellen und Nachweise

ORD-Eintrag
ord-4eba50608b1e40a98a70d53d19779849
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388166B2

Notizen zur Reaktion

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