Diethyl Ether → 1-(Pyridin-2-yl)propan-2-one
Reaction equation
C([Li])CCC.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].C(#N)C.[CH2:16]([O:18]CC)[CH3:17]>>[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:16]([CH3:17])=[O:18]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 960 mg of n-butyllithium in diethyl ether was added dropwise 1480 μl of α-picoline at 0° C. under an argon and the reaction mixture was stirred for 10 minutes at 0° C. To the reaction mixture was added 782 l of acetonitrile and the mixture was stirred for 3 hours at room temperature, followed by extraction with 30 ml of 1.5N-sulfuric acid. The acidic solution was washed with 25 ml of diethyl ether, and made alkaline with a 2N-aqueous sodium hydroxide solution and the solution was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residual oil was distilled under reduced pressure to give 700 mg of methyl 2-pyridylmethyl ketone as an oil.
Workup
- stirringthe mixture was stirred for 3 hours at room temperature
- extractionfollowed by extraction with 30 ml of 1.5N-sulfuric acid
- washThe acidic solution was washed with 25 ml of diethyl ether
- extractionthe solution was extracted with dichloromethane
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- distillationThe residual oil was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-4e405fa4807245b998e93638036fe388
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04877795
Reaction notes
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