Ethyl Acetate → HCID 70873815, Verbindung

HRID 2208920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208920
[OH:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][CH2:24][OH:25].C(OCC)(=O)C>C(#N)C.O>[OH:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoate

Produkt 1

HCID 70873815HCID 70873815, VerbindungAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of methyl 5-hydroxy-2-methyl-3-nitrobenzoate (1.5 g, 7.1 mmol) in ACN (15 mL), were added cesium carbonate (4.6 g, 14 mmol) and 2-bromoethanol (2.5 mL, 35 mmol). The resulting reaction mixture was heated at 80° C. overnight. On completion, the reaction mixture was diluted with water and extraction was carried out using ethyl acetate. The combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to afford the title compound (1.35 g, 74%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe combined organic layers were washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dbb75da19b1643d8af6cccf02d70ae64
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376422B2

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