Methyl iodide → 1,3,4-Trimethylpyridin-1-ium iodide
Reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[CH3:9][I:10]>CC(C)=O>[I-:10].[CH3:9][N+:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As shown in Scheme 2 (in FIG. 2), a solution of 100 g of 3,4-dimethylpyridine in 800 ml of acetone was added dropwise to 57.27 mL of methyl iodide. The reaction mixture was stirred at room temperature for 18 hrs. The solid was collected by filtration and washed with cold ether. After drying under vacuum, there was obtained 202 g of 1,3,4-trimethylpyridinium iodide. The subsequent Grignard reaction was conducted under standard conditions to afford an unstable intermediate that was utilized immediately.
Workup
- filtrationThe solid was collected by filtration
- washwashed with cold ether
- customAfter drying under vacuum
Sources & evidence
- ORD record
- ord-ce38c26ff9634aa1870c0c0115da3771
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05354758
Reaction notes
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