Diethyl Ether → 2-Propyl-4-chloro-3-methyl-pyridine

HRID 1635093Notes

Reaction equation

HRID 1635093 reaction equation
[CH2:1](I)[CH2:2][CH3:3].[Li].[Cl:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[CH3:13].CCOCC>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:1]([C:9]1[C:8]([CH3:13])=[C:7]([Cl:6])[CH:12]=[CH:11][N:10]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 336431-IodopropaneHCID 27577094-Chloro-3-methylpyridineHCID 3028194Lithium2×

Product 1

HCID 186758642-Propyl-4-chloro-3-methyl-pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of propyl iodide (12.7 g) in THF (10 ml) is added lithium (0.45 g) and the reaction is allowed to stir at room temperature until complete dissolution of the lithium. 4-Chloro-3-methyl-pyridine (9.5 g) is then added and the mixture allowed to stir at 40° C. for 4 hours. After cooling at room temperature, ether is added and the organic phase washed with water. After removal of the solvent the desired product is obtained by chromatography using hexane/ether 9/1 as solvent.

Workup

  1. temperatureAfter cooling at room temperature
  2. washthe organic phase washed with water
  3. customAfter removal of the solvent the desired product
  4. customis obtained by chromatography

Sources & evidence

ORD record
ord-9b2234da1006484a9b09cfdc7d89fb83
Source dataset
uspto-grants-2003_01
Patent number
US06509349B1

Reaction notes

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