Potassium Carbonate → Triacetylresveratrol

HRID 1163276Notes

Reaction equation

HRID 1163276 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:10]=1)(=[O:3])[CH3:2].[C:16]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH2:25])=[CH:22][CH:21]=1)(=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C(=NO)(C1C=CC=CC=1)C>[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:25]=[CH:24]/[C:23]2[CH:26]=[CH:27][C:20]([O:19][C:16](=[O:18])[CH3:17])=[CH:21][CH:22]=2)[CH:8]=[C:9]([O:11][C:12](=[O:14])[CH3:13])[CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 69185AcetophenonoximeHCID 758214-Ethenylphenyl acetateHCID 686482403,5-Diacetoxybromobenzene

Product 1

HCID 5962587Triacetylresveratrol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A 10 ml Schlenk tube equipped with a magnetic stirrer is charged with 218 mg (0.8 mmol) 3,5-diacetoxybromobenzene, 136 mg (0.84 mmol) 4-acetoxystyrene, 187 mg potassium carbonate (0.9 mmol) and 0.22 mg (0.1 mol %) of the acetophenon-oxim derived palladium catalyst CAS No. 32679-19-9 as used in Example 9. The tube was evacuated and flushed with argon three times and 1 ml de-aerated DMF was added under inert conditions. The reaction was carried out under stirring for 15 hours at 150° C. Work-up was conducted following the procedure of Example 4 and to give (E)-3,4′,5-triacetoxystilbene.

Workup

  1. customA 10 ml Schlenk tube equipped with a magnetic stirrer
  2. customThe tube was evacuated
  3. customflushed with argon three times and 1 ml de-aerated DMF
  4. additionwas added under inert conditions

Sources & evidence

ORD record
ord-2407f36fd476426987f9eb0da100a3f0
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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