Potassium Carbonate → HCID 18653278, compound

HRID 1109652Notes

Reaction equation

HRID 1109652 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([OH:31])[C:28]=1[O:29][CH3:30])/[CH:6]=[C:7]1/[C:8]([O:10][CH2:11][C@H:12]/1[CH2:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1)=[O:9].[N+:32]([C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1)([O-:34])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH2:39][C:38]2[CH:41]=[CH:42][C:35]([N+:32]([O-:34])=[O:33])=[CH:36][CH:37]=2)[C:28]=1[O:29][CH3:30])/[CH:6]=[C:7]1/[C:8]([O:10][CH2:11][C@H:12]/1[CH2:13][C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=1)=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 86747916HCID 86747916, compound

Product 1

HCID 18653278HCID 18653278, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (S)-(E)-2-(3,4-dimethoxy-5-hydroxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide (7.5 g, 17.4 mmol), p-nitrobenzyl bromide (4.6 g, 21.3 mmol) and potassium carbonate (3.0 g, 21.7 mmol) in 100 ml of acetone was heated under reflux for 3.5 hours. After the solvent was distilled off under reduced pressure, the residue was added with water and then ethyl acetate. The organic layer was washed successively with 2N-HCl, water, saturated NaHCO3 and saturated NaCl and then, dried over anhydrous magnesium sulfate. The solvent was thereafter distilled off. The residue thus obtained was purified by column chromatography, whereby 9 g of the title compound were obtained as colorless foam (yield: 91%).

Workup

  1. temperatureunder reflux for 3.5 hours
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. additionthe residue was added with water
  4. washThe organic layer was washed successively with 2N-HCl, water, saturated NaHCO3 and saturated NaCl
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was thereafter distilled off
  7. customThe residue thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-67e4dc0d5436494caddb074bad56c64f
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

Loading…