Sodium Hydroxide → 5-Ethynyl-2,3-dimethoxypyridine
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]#[C:12][Si](C)(C)C)=[CH:5][N:4]=1.[OH-].[Na+]>CO>[C:11]([C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1)#[CH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-Dimethoxy-5-[(trimethylsilyl)ethynyl]pyridine (Intermediate 31) (9.8 g, 42 mmol) was dissolved in a mixture of aqueous sodium hydroxide (21 ml, 2 M, 42 mmol) and methanol (50 ml) to give a colourless solution which was stirred for 16 hours. The reaction was evaporated and the residue was partitioned between ethyl acetate and water before the organic layer was dried and concentrated in vacuo. The crude material was purified by (SiO2; 0-10% ethyl acetate in petrol) to afford 5-ethynyl-2,3-dimethoxypyridine (5.6 g, 82%).
Workup
- customto give a colourless solution which
- customThe reaction was evaporated
- customthe residue was partitioned between ethyl acetate and water before the organic layer
- customwas dried
- concentrationconcentrated in vacuo
- customThe crude material was purified by (SiO2; 0-10% ethyl acetate in petrol)
Sources & evidence
- ORD record
- ord-7a477c5919c743b684e780b8f7c73222
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09180122B2
Reaction notes
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