HCID 86757551, compound → HCID 18362039, compound

HRID 382820Notes

Reaction equation

HRID 382820 reaction equation
[C:1]([C:14]1[CH:15]=[C:16]([C:33]([O:35]C)=[O:34])[N:17]([CH2:19][C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30]CC)=[O:29])=[CH:22][CH:21]=2)[CH:18]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>C1COCC1.[Pd]>[C:28]([CH2:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:17]2[CH:18]=[C:14]([C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:15]=[C:16]2[C:33]([OH:35])=[O:34])=[CH:21][CH:22]=1)([OH:30])=[O:29]

Participants

5

Reactant 2

HCID 86757551HCID 86757551, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18362039HCID 18362039, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

50 mg (0.1 mmol) of methyl (E)-4-dodecanoyl-1-{4-[2-(ethoxycarbonyl)ethenyl]benzyl}pyrrole-2-carboxylate are dissolved in 5 ml of THF. After addition of a spatula tip of Pd/C, hydrogenation is carried out with vigorous stirring at room temperature under a hydrogen atmosphere produced using a hydrogen-filled balloon fitted onto the reaction flask for 4 h. Addition of kieselguhr is followed by filtration, the solvent is distilled off, the residue is mixed with 12 ml of ethanol and 4 ml of 10% strength aqueous KOH, and the resulting mixture is boiled under reflux for 1 h. Cooling is followed by dilution with water, acidification with dilute HCl and extraction with ether. The organic phase is washed with dilute HCl, dried over Na2SO4 and concentrated. The product is precipitated from petroleum ether.

Workup

  1. customproduced
  2. additionfilled balloon
  3. customfitted onto the reaction flask for 4 h
  4. additionAddition of kieselguhr
  5. filtrationis followed by filtration
  6. distillationthe solvent is distilled off
  7. additionthe residue is mixed with 12 ml of ethanol and 4 ml of 10% strength aqueous KOH
  8. temperatureunder reflux for 1 h
  9. temperatureCooling
  10. extractionis followed by dilution with water, acidification with dilute HCl and extraction with ether
  11. washThe organic phase is washed with dilute HCl
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated
  14. customThe product is precipitated from petroleum ether

Sources & evidence

ORD record
ord-ec8a48a2472d4babad3105bab07fe0df
Source dataset
uspto-grants-2001_10
Patent number
US06310217B1

Reaction notes

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