Potassium Carbonate → HCID 69529373, compound

HRID 1634895Notes

Reaction equation

HRID 1634895 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(OP([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(OCC)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:18]=[C:17]([CH:19]=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:16]=[CH:15][N:14]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13345Triethyl phosphonoacetateHCID 186750102-(3,4,5-Trimethoxyphenyl)pyridine-4-carboaldehyde

Product 1

HCID 69529373HCID 69529373, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

2-(3,4,5-Trimethoxyphenyl)pyridine-4-carboaldehyde (507 mg) and ethyl diethylphosphonoacetate (570 μL) were dissolved in tert-butanol (16 mL), and to the solution potassium carbonate (438 mg) was added. The mixture was stirred for 3 hours under reflux and concentrated under reduced pressure. The residue was dissolved in chloroform, and the solution was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washthe solution was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c634ae911fff4c32b5ded475a6b1c7d9
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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