Water → 6-(Methylthio)-3-pyridinecarboxaldehyde
Reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1.[CH3:10][S-:11].[Na+].O>CN(C=O)C>[CH3:10][S:11][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In DMF (5.0 mL) was dissolved 6-chloronicotinaldehyde (300 mg, 2.12 mmol). Sodium thiomethoxide (178 mg, 2.54 mmol) was added and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 6-(methylthio)nicotinaldehyde (239 mg, 74%).
Workup
- extractionExtraction with ethyl acetate
- washwashing with saturated brine
- dry with materialdrying over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-bede641e31474cfdb4de9d5e028b3bb0
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150569B2
Reaction notes
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