Ethyl Acrylate → HCID 66960160, Verbindung

HRID 1446465Notizen

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C=O)C>[CH2:18]([O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1)[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a DMF (20 mL) solution of 5-bromo-3-methoxy-2-nitropyridine (726 mg) synthesized according to the method described in Acta Chemica Scandinavica vol. 47, p. 805, 1993, ethyl acrylate (0.44 mL), palladium acetate (35 mg), 2-(di-tert-butylphosphino) biphenyl (93 mg) and TEA (0.87 mL) were added, and the reaction solution was agitated at 80° C. for 3 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution to separate an organic layer. After the obtained organic layer was dried over anhydrous magnesium sulfate, solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 2:1), and 787 mg (69%) of (E)-3-(5-methoxy-6-nitropyridin-3-yl)acrylic acid ethyl ester was obtained. The physical properties of the compound are as follows.

Aufarbeitung

temperatureto be cooled to room temperature
customto separate an organic layer
dry with materialAfter the obtained organic layer was dried over anhydrous magnesium sulfate, solvent
customwas evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag: ord-4a1c411735284e9e8f36794dd506720d
Quelldatensatz: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07667041B2

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