Diethyl Ether → 1-(Pyridin-2-yl)undecan-1-one
Reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)#N.[Cl-].[NH4+].C([O:25]CC)C>>[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)(=[O:25])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Procedure
To 100 ml of anhydrous ether was added 3.60 g of magnesium for Grignard reaction, and to the mixture was added while stirring 36.5 g of 1-bromodecane. After the magnesium was completely dissolved, a diethyl ether solution of 15.6 g (0.15 mol) of 2-cyanopyridine was added dropwise, and the mixture was refluxed for 7 hours. After cooling, saturated ammonium chloride solution was added, the diethyl ether layer was separated, and the aqueous layer was further extracted with diethyl ether. The ether layers were combined, washed with water, and then dried over anhydrous sodium sulfate. After concentration under a reduced pressure, the residue was purified by separation according to silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 21.6 g of the desired product (yield 58.3%).
Workup
- customfor Grignard reaction
- additionto the mixture was added
- temperaturethe mixture was refluxed for 7 hours
- temperatureAfter cooling
- customthe diethyl ether layer was separated
- extractionthe aqueous layer was further extracted with diethyl ether
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationAfter concentration under a reduced pressure
- customthe residue was purified by separation
Sources & evidence
- ORD record
- ord-f9567617c20c4dd59a147ba5286b6cb6
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05219847
Reaction notes
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