Dimethyl Sulfate → (1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

HRID 520788Notes

Reaction equation

HRID 520788 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:25])[CH2:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)=[CH:4][C:3]=1[O:26][CH3:27].[C:28]([O-])([O-])=O.[K+].[K+].COS(=O)(=O)OC>CC(C)=O.O>[CH3:27][O:26][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10](=[O:25])[CH2:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH:6]=[CH:7][C:2]=1[O:1][CH3:28]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 969516Curcumin

Product 1

HCID 10249311(1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dioneYield 44.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To the solution of (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (368 mg, 1.0 mmol, 1.0 eq.) in dry acetone (10 mL) were added anhydrous K2CO3 (138 mg, 1.0 mmol, 1.0 eq.) and sulfuric acid dimethyl ester (176 mg, 1.0 mmol, 1.0 eq.) at rt. The reaction mixture was heated under reflux overnight, cooled, diluted with water and extracted with CH2Cl2 (30 mL×3). The combined organic layers were washed with H2O, dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by silica column chromatography using CH2Cl2 as eluent to provide (1E,6E)-1-(3,4-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (170 mg, 44%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. extractionextracted with CH2Cl2 (30 mL×3)
  5. washThe combined organic layers were washed with H2O
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-3e7a97d868ea4569a5f92d9f76263601
Source dataset
uspto-grants-2016_05
Patent number
US09328081B2

Reaction notes

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