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

HRID 659053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659053
[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 rt, 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-8201c766f1c3470e9d7ab512b5e95e41
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080563B2

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