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

HRID 1163270Notes

Reaction equation

HRID 1163270 reaction equation
[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]

Participants

7

Reactant 3

HCID 74726Phenol, 4-bromo-, 1-acetateHCID 516892Sodium BicarbonateHCID 113105593,5-Diacetoxy Styrene

Product 1

HCID 5962587Triacetylresveratrol

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

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.

Workup

  1. customA flask equipped with magnetic stirrer
  2. customthe mixture was flushed with argon
  3. customevacuated

Sources & evidence

ORD record
ord-c1bbab8e0da74da3ae16839899640c2c
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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