Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](C#N)=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20]>>[CH3:12][N:13]1[C:17]([C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20]Participants
Procedure
A mixture of 5.0 g (0.034 mole) of 4-methylbenzoylcyanide and 0.8 g (0.005 mole) of methyl 1-methyl-pyrrole-2-acetate was added over 4 hours from a heated addition funnel to a sample of 3.8 g (0.025 mole) of methyl 1-methylpyrrole-2-acetate at 180° through which nitrogen was bubbled. The mixture was heated for six more hours after the addition was complete. The reaction was cooled and dissolved in methylene chloride-toluene. The organic solution was washed with 10 percent sodium hydroxide solution and saturated brine and dried (MgSO4). The solvent was evaporated in vacuo and the residue recrystallized twice from methanol to give 5.41 g (69 percent yield) of white crystalline methyl 1-methyl-5-(4-methyl-benzoyl)-pyrrole-2-acetate, mp 118°-120° C. The solid state IR spectrum was identical to authentic material.
Workup
- customwas bubbled
- temperatureThe mixture was heated for six more hours
- additionafter the addition
- temperatureThe reaction was cooled
- dissolutiondissolved in methylene chloride-toluene
- washThe organic solution was washed with 10 percent sodium hydroxide solution and saturated brine
- dry with materialdried (MgSO4)
- customThe solvent was evaporated in vacuo
- customthe residue recrystallized twice from methanol
Sources & evidence
- ORD record
- ord-6485920042fe41719bbc666e5ea2aa49
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04255335
Linked notes
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