Potassium Carbonate → trans-3,5,3',4'-Tetraacetoxystilbene

HRID 1163274Notes

Reaction equation

HRID 1163274 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7](Br)[CH:8]=[CH:9][C:10]=1[O:11][C:12](=[O:14])[CH3:13])(=[O:3])[CH3:2].[C:16]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:28][C:29](=[O:31])[CH3:30])[CH:27]=1)[CH:23]=[CH2:24])(=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].C(=NO)(C1C=CC=CC=1)C>[Pd]>[C:16]([O:19][C:20]1[CH:21]=[C:22](/[CH:23]=[CH:24]/[C:7]2[CH:8]=[CH:9][C:10]([O:11][C:12](=[O:14])[CH3:13])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH:25]=[C:26]([O:28][C:29](=[O:31])[CH3:30])[CH:27]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 69185AcetophenonoximeHCID 113105593,5-Diacetoxy StyreneHCID 124332983,4-Diacetoxybromobenzene

Product 1

HCID 13887316trans-3,5,3',4'-Tetraacetoxystilbene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A 10 ml Schlenk tube equipped with magnetic stirrer is charged with 218 mg (0.8 mmol) 3,4-diacetoxybromobenzene, 176 mg (0.84 mmol) 3,5-diacetoxystyrene, 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 with stirring for 19 hours at 150° C. Work-up was conducted following the procedure of Example 5 and to give (E)-3,3′, 4′,5-tetraacetoxystilbene.

Workup

  1. customA 10 ml Schlenk tube equipped with 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-415196c5c8514b4dab4b37d120f56e33
Source dataset
uspto-grants-2010_10
Patent number
US07820848B2

Reaction notes

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