Ethanol → HCID 21480996, compound

HRID 1490330Notes

Reaction equation

HRID 1490330 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][CH2:12][CH:13](C(OCC)=O)C(OCC)=O)=[C:5]([N:24]2[CH:28]=[CH:27][CH:26]=[CH:25]2)[CH:4]=1.[OH-:29].[Na+].[CH2:31]([OH:33])[CH3:32]>>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][CH2:12][C:13]([O:33][CH2:31][CH3:32])=[O:29])=[C:5]([N:24]2[CH:25]=[CH:26][CH:27]=[CH:28]2)[CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54292647HCID 54292647, compound

Product 1

HCID 21480996HCID 21480996, compound

Conditions

Temperature
150 °C

Procedure

In 50 ml of ethanol was dissolved 3.1 g of diethyl (2-(4,5-dimethoxy-2-(1-pyrrolyl)phenyl)ethyl)malonate, and 5.0 ml of 35% sodium hydroxide was added to the solution, followed by heating under reflux for 3 hours. The solvent was removed under reduced pressure, and water was added to the residue. The residue was made acidic with concentrated hydrochloric acid and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to yield pale brown powder. The powder was heated at 150° C. for 10 minutes, allowed to cool, and purified by silica gel column chromatography (chloroform-methanol) to obtain 2.1 g of pale brown powder. Recrystallization from chloroform-ethyl ether gave the title compound as a colorless crystal.

Workup

  1. additionwas added to the solution
  2. temperatureby heating
  3. temperatureunder reflux for 3 hours
  4. customThe solvent was removed under reduced pressure, and water
  5. additionwas added to the residue
  6. extractionextracted with chloroform
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto yield pale brown powder
  10. temperatureto cool
  11. custompurified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-344a1a2d433f4ff08695cbc365fdd0a9
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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