Water → 5-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine

HRID 1789168Notes

Reaction equation

HRID 1789168 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.[H-].[Na+].O>CN(C=O)C>[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

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 788945-Ethyl-2-pyridineethanol

Product 1

HCID 133148065-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridineYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 minutes, poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4). The solvent was evaporated off to give 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene as crystals (62.0 g, 62.9%). Recrystallization from ether-hexane gave colorless prisms, m.p. 53°-54° C.

Workup

  1. temperaturecooling for one hour
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-0ed7cb4f3509415b89681d4cddec3600
Source dataset
uspto-grants-1987_08
Patent number
US04687777

Reaction notes

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