Phenol, 4-bromo-, 1-acetate → Triacetylresveratrol

HRID 1163270

Reaktionsgleichung

[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)[CH:8]=[CH2:9])(=[O:3])[CH3:2].[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=1)(=[O:19])[CH3:18].C([O-])(O)=O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:8]=[CH:9]/[C:24]2[CH:25]=[CH:26][C:21]([O:20][C:17](=[O:19])[CH3:18])=[CH:22][CH:23]=2)[CH:10]=[C:11]([O:13][C:14](=[O:16])[CH3:15])[CH:12]=1)(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A flask equipped with magnetic stirrer was charged with 50 mg (0.23 mmol, 1 eq) of 3,5-diacetoxystyrene, 49 mg (0.23 mmol) of 4-acetoxybromobenzene, 46 mg (0.27 mmol) of NaHCO3 and 78 mg (0.54 mmol, 2.4 eq) of tetrabutylammoniumchloride. The reactants were suspended in 2 ml DMF and the mixture was flushed with argon and then evacuated. The argon flushing and evacuation procedure was carried out three times. The reaction was started by adding 0.76 mg of palladium acetate in 50 μl of de-aerated DMF (3 μmol, 1.5 mol %), and stirred at 100° C. for three hours. Work-up of the reaction mixture following the procedure of Example 5 gave (E)-3,4′,5-triacetoxystilbene.

Aufarbeitung

customA flask equipped with magnetic stirrer
customthe mixture was flushed with argon
customevacuated

Quellen und Nachweise

ORD-Eintrag: ord-c1bbab8e0da74da3ae16839899640c2c
Quelldatensatz: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07820848B2

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