Methyl 4-tridecanoylpyrrole-2-carboxylate → Methyl 4-tridecylpyrrole-2-carboxylate
Reaction equation
[C:1]([C:15]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[NH:18][CH:19]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>[Ni].C(O)C>[CH2:1]([C:15]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[NH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
Into a mixture of 150 ml of Raney nickel (activated type, produced by Aldrich Co.), which had been washed with water and then ethanol, and 750 ml of ethanol, was added 15.06 g (37.9 mmol) of dithioethyleneketal of methyl 4-tridecanoylpyrrole-2-carboxylate obtained in Synthesis Example 2. The mixture was refluxed for 30 minutes and cooled to about 30° C. After removing Raney nickel, the mixture was evaporated. The residue was recrystallized from ethanol to obtain 10.70 g of methyl 4-tridecylpyrrole-2-carboxylate as white crystals. The yield was 91.8% and the melting point was 80° to 82° C.
Workup
- washhad been washed with water
- customobtained in Synthesis Example 2
- temperatureThe mixture was refluxed for 30 minutes
- customAfter removing Raney nickel
- customthe mixture was evaporated
- customThe residue was recrystallized from ethanol
Sources & evidence
- ORD record
- ord-e0c14aff3eaa4a4dbb4c55657e53dbab
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05153217
Reaction notes
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