2-Methylpyridine → HCID 12094214, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH:13]1([C:17](=[O:16])[CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:14][CH2:15][CH2:11][CH2:10][CH2:9][CH2:8]1Participants
Conditions
- Temperature
- -78 °C
Procedure
A 100 mL round bottom flask was charged with 2-picoline (2.52 mL, 25.5 mmol) and anhydrous THF (30 mL). The solution was cooled to −78° C. and n-butyllithium (17.5 mL of a 1.6 M solution in THF, 28.05 mmol) was added dropwise to the solution. After addition was complete, the reaction was warmed slowly to room temperature over one hour and then cooled again to −78° C. N-methoxy-N-methyl cycloheptyl amide (5.0 g, 27.03 mmol, formed above) was added to the reaction. The reaction mixture was allowed to warm to room temperature with stirring overnight. The reaction was carefully quenched with water and extracted with ethyl acetate. The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (ethyl acetate:hexane, 3:7, silica gel) to provide 1-cycloheptyl-2-(2-pyridyl)ethan-1-one (5.03 g, 91%)
Workup
- additionAfter addition
- temperaturethe reaction was warmed slowly to room temperature over one hour
- temperaturecooled again to −78° C
- temperatureto warm to room temperature
- customThe reaction was carefully quenched with water
- extractionextracted with ethyl acetate
- dry with materialThe organic extracts were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue was purified by flash chromatography (ethyl acetate:hexane, 3:7, silica gel)
Sources & evidence
- ORD record
- ord-51fd262285bd46e28f32da1f331f7d16
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06436964B1
Reaction notes
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