Water → HCID 68957153, Verbindung

HRID 390650

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:15])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1OCCC.[CH3:20][NH:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.O>CN(C)C=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15]/[C:9](=[CH:8]\[C:5]1[CH:4]=[CH:3][C:2]([C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:21][CH3:20])[CH:27]=2)=[CH:7][CH:6]=1)/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

1.6 g (4.3 mmol) of ethyl (E)-3-(4-iodo-3-propoxyphenyl)-2-methylacrylate are dissolved in 10 mL of a 4/1v/v mixture of dimethylformamide and of aqueous 2 M potassium phosphate solution. 0.9 g (5.7 mmol) of 3-methylaminophenylboronic acid prepared as described in Example 31e, 58 mg (0.2 mmol) of palladium acetate and 152 mg (0.4 mmol) of dicyclohexylbiphenylphosphine are added. The mixture is stirred for 3 hours at 90° C. After cooling and adding water, the medium is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 1.0 g (65%) of ethyl (E)-2-methyl-3-(3′-methylaminobiphenyl-4-yl)acrylate is obtained.

Aufarbeitung

additionare added
temperatureAfter cooling
extractionthe medium is extracted with ethyl acetate
washThe organic phase is washed with saturated sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue obtained
customis purified by chromatography on a column of silica
washeluted with an 8/2 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag: ord-e1edcaf21acc4dd19f211f0a5f40af81
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08383652B2

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