Methyl 4-tridecanoylpyrrole-2-carboxylate dithioethylene ketal → Methyl 4-tridecylpyrrole-2-carboxylate

HRID 129341Notes

Reaction equation

HRID 129341 reaction equation
C1SSO[C:4]([C:7]2[NH:8][CH:9]=[C:10]([C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:11]=2)([O:5]C)[O:3][CH2:2]1>[Ni].C(O)C>[CH2:12]([C:10]1[CH:11]=[C:7]([C:4]([O:3][CH3:2])=[O:5])[NH:8][CH:9]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 86745413Methyl 4-tridecanoylpyrrole-2-carboxylate dithioethylene ketal

Product 1

HCID 15023274Methyl 4-tridecylpyrrole-2-carboxylateYield 91.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

Methyl 4-tridecanoylpyrrole-2-carboxylate dithioethylene ketal (15.06 g, 37.9 mmol) prepared in Synthetic Example 8 was added to a mixed solution of 750 ml of ethanol and 150 ml of Raney-nickel (activated type, manufactured by Aldrich Co.) which was washed with water and ethanol successively. The mixture was heated under reflux for 30 minutes. After cooling it to ca. 30° C., the Raney-nickel was filtered off and the filtrate was concentrated under reduced pressure. Recrystallization of the residue from ethanol gave 10.70 g (91.8% yield) of methyl 4-tridecylpyrrole-2-carboxylate as white crystals, m.p. 80°-82° C.

Workup

  1. washwas washed with water and ethanol successively
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. filtrationthe Raney-nickel was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-d6ef59bab40f423b866a72a12fadbdaf
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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