Water → {4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051225
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Si](C)(C)C)=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[C:25]=1[CH:26]=[O:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:26]([C:25]2[C:28]([O:32][CH3:33])=[CH:29][CH:30]=[CH:31][C:24]=2[Cl:23])[OH:27])=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 109649712-Chloro-6-methoxybenzaldehydeHCID 90102892HCID 90102892, Verbindung

Produkt 1

HCID 90103009{4-[2-(2-Chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl esterAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of (3-nitro-4-trimethylsilanylmethyl-phenyl)-carbamic acid tert-butyl ester (1.00 g, 3.08 mmol) and 2-chloro-6-methoxybenzaldehyde (526 mg, 3.08 mmol) in THF (10 mL) was added tetra-butylammonium fluoride (121 mg, 462 μmol) at 25° C., the color of the solution changed to dark blue after the addition. The reaction mixture was stirred at 25° C. for 30 min and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded {4-[2-(2-chloro-6-methoxy-phenyl)-2-hydroxy-ethyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (0.45 g, 35%) as an oil.

Aufarbeitung

  1. additionafter the addition
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. concentrationfollowed by concentration in vacuo
  7. customgave a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-08224acda1144e04b13f781ee1117470
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388166B2

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