Iodoethane → 5-Ethoxy-2-methylpyridine
Reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH2:11](I)[CH3:12]>CN(C)C=O.O>[CH2:11]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)[CH3:12]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred suspension of 16.6 g sodium hydride in 500 ml dry dimethylformamide (DMF) under nitrogen at 0° C. is added 90 g 5-hydroxy-2-methylpyridine at such a rate that the temperature remains between 0°-5° C. When gas evolution ceases, 73.8 ml ethyl iodide in 100 ml DMF is added dropwise. After stirring at room temperature overnight, the mixture is diluted with water and extracted with ether. The ether extracts are washed with brine, dried and concentrated. This oil is distilled to give 62.5 g of 5-ethoxy-2-methylpyridine, bp 89°-91° C. at 12 mm.
Workup
- customremains between 0°-5° C
- extractionextracted with ether
- washThe ether extracts are washed with brine
- customdried
- concentrationconcentrated
- distillationThis oil is distilled
Sources & evidence
- ORD record
- ord-d3a3be1a74014303823469acddf2dc76
- Source dataset
- uspto-grants-1989_01
- Patent number
- US04798619
Reaction notes
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