Bromocyclopentane → Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

HRID 1095762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095762
[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].Br[CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:18]1([O:1][C:2]2[C:3]([N+:14]([O-:16])=[O:15])=[C:4]([CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])[CH2:22][CH2:21][CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 59268115Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate

Produkt 1

HCID 66781723Methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-hydroxy-4-methoxy-2-nitrobenzoate (1.14 g, 5.0 mmol), bromocyclopentane (0.7 mL, 6.5 mmol), potassium carbonate (2.0 g, 14 mmol), and anhydrous acetonitrile (15 mL) was refluxed under N2. After 19 h, the reaction was allowed to cool to room temperature, concentrated, and purified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate) to give methyl 3-(cyclopentyloxy)-4-methoxy-2-nitrobenzoate: MS (ESI): 296.5.

Aufarbeitung

  1. temperaturewas refluxed under N2
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (4:1→3:2; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d65596030e66412eaecd3601da7b1681
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138205B2

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