p-Fluoronitrobenzene → 5-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine

HRID 1743334Notes

Reaction equation

HRID 1743334 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 788945-Ethyl-2-pyridineethanol

Product 1

HCID 133148065-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-ethyl-2-pyridyl)ethanol (12 g) and 4-fluoronitrobenzene (11.2 g) in dimethylformamide (80 ml) sodium hydride (3.9 g) is added portionwise under ice cooling. This mixture is agitated under ice cooling for one hour, at room temperature for thirty minutes, poured into ice water and extracted with ethyl acetate. Drying the organic layer and evaporating the solvent gives a yellow solid (4-(2-(5-ethyl-2-pyridyl)ethoxy)nitrobenzene, 21.4 g, 98.2%). Recrystallizing from a mixture of ether and hexane yields pale yellow crystals (m.p. 45–47° C.). NMR δ (ppm) in CDCl3: 1.25 (3H, t, J=7.6), 2.65 (2H, q, J=7.6), 3.28 (2H, t, J=6.7), 4.47 (2H, t, J=6.7), 6.95 (2H, m), 7.19 (1H, d, J=7.9), 7.49 (1H, dd, J=2.4; 8.0), 8.17 (2H, m), 8.41 (1H, d, J=2.2).

Workup

  1. extractionextracted with ethyl acetate
  2. customDrying the organic layer
  3. customevaporating the solvent

Sources & evidence

ORD record
ord-7431e072a7044127a3a9c8b7e2d2eb2f
Source dataset
uspto-grants-2006_03
Patent number
US07009057B2

Reaction notes

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