Potassium Carbonate → Benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate

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Reaktionsgleichung

Br[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][C:4]=1[N+:19]([O-:21])=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:41]([C:43]1[C:48]([CH3:49])=[CH:47][C:46](/[CH:50]=[CH:51]/[C:52]([O:54][CH3:55])=[O:53])=[CH:45][C:44]=1[CH3:56])=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:55][O:54][C:52](/[CH:51]=[CH:50]/[C:46]1[CH:45]=[C:44]([CH3:56])[C:43](/[CH:41]=[CH:2]/[C:3]2[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])=[CH:5][C:4]=2[N+:19]([O-:21])=[O:20])=[C:48]([CH3:49])[CH:47]=1)=[O:53]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of benzyl 4-bromomethyl-3-nitrobenzoate (2.06 g, 5.88 mmol) and triphenylphosphine (1.54 g, 5.87 mmol) in DMF (10 mL) was heated at 100° C. for 1 h. To this solution was added methyl (E)-3-(4-formyl-3,5-dimethylphenyl)-acrylate (1.28 g., 5.86 mmol) and potassium carbonate (1.63 g, 11.8 mmol) and the mixture was heated and stirred at 100° C. for 18 h. The reaction was poured into ethyl acetate and extracted with water once and brine.five times. The organic layer was dried, filtered, and the solvent was removed under reduced pressure. The residue was purified by chromatography using a 0-40% gradient of heptane/ethyl acetate to give benzyl 4-{(E)-2-[4-((E)-2-methoxycarbonylvinyl)-2,6-dimethylphenyl]-vinyl}-3-nitrobenzoate.

Aufarbeitung

temperaturethe mixture was heated
extractionextracted with water once
customThe organic layer was dried
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag: ord-4d150cd586684b02b165da635af1bda0
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08222248B2

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