Hydrochloric Acid → HCID 54292647, compound

HRID 1490329Notes

Reaction equation

HRID 1490329 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11]O)=[C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:4]=1.Cl.[C:19](=[O:22])([O-:21])[O-].[Na+].[Na+].[Na].[C:26]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:27][C:28]([O-])=O.[CH2:35](OCC)[CH3:36]>C(O)C.O1CCCC1.O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH2:11][CH2:28][CH:27]([C:26]([O:32][CH2:33][CH3:34])=[O:31])[C:19]([O:21][CH2:35][CH3:36])=[O:22])=[C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:4]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 21480992HCID 21480992, compound

Product 1

HCID 54292647HCID 54292647, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 15 ml of ethyl ether was dissolved 3.0 g of 4,5-dimethoxy-2-(1-pyrrolyl)benzenemethanol, and 15 ml of concentrated hydrochloric acid was added thereto, followed by stirring at room temperature for 1 hour. To the reaction mixture was added 50 ml of water, and the mixture was neutralized with a saturated sodium carbonate aqueous solution and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to yield a brown oily substance. Separately, 460 mg of metallic sodium was dissolved in 25 ml of ethanol, and 6.18 g of ethyl malonate was added thereto to prepare a solution. To this solution was added a tetrahydrofuran solution (25 ml) of the above-prepared brown oily substance. After stirring at room temperature for 3 hours, the solvent was removed under reduced pressure. Water was added to the residue, and the mixture was made acidic with concentrated hydrochloric acid and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification of the residue by silica gel column chromatography (chloroform) gave 3.10 g of the title compound as a brown oily substance.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customto yield a brown oily substance
  6. customto prepare a solution
  7. stirringAfter stirring at room temperature for 3 hours
  8. customthe solvent was removed under reduced pressure
  9. additionWater was added to the residue
  10. extractionextracted with chloroform
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customPurification of the residue by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-57310ddd10584069abd6c8786eb8815b
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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