Toluene → Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-phenylbenzoate

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Reaktionsgleichung

[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:10]=[C:11]([CH:16]=1)C(OC)=O.[C:35](=[O:38])([O-])[O-:36].[Na+].[Na+].[Cl-].[Li+].[C:43]1(B(O)O)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[C:52]1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:25]([O:32][CH3:33])=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[C:11]([CH:16]=1)[C:35]([O:36][CH3:52])=[O:38]

Komponenten

Reaktionsbedingungen

Temperatur: 95 °C

Versuchsvorschrift

To a solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-3-(trifluoromethanesulfonyl)oxybenzoate (444 mg, 0.8740 mmol) in toluene (12 ml) were added tetrakistriphenylphosphine palladium (60 mg, 0.0519 mmol), aqueous solution of sodium carbonate (2M aqueous solution, 1.35 ml), lithium chloride (89 mg, 2.0995 mmol) and ethanolic solution (2.1 ml) of benzeneboronic acid (320 mg, 2.6244 mmol) and the mixture was heated with stirring at 95° C. for 16 hours. The reaction solution was diluted with ethyl acetate (100 ml), washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (349 mg, 0.8004 mmol, 68%).

Aufarbeitung

temperaturethe mixture was heated
washwashed with water
customdried
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag: ord-df42afa5fa594bc2a5d3f031aa195b4e
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07122543B2

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