4-Fluorobenzonitrile → 4-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

HRID 377124

Reaction equation

HRID 377124 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[H-].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 702836-Methylpyridine-2-ethanol

Product 1

HCID 142112794-[2-(6-Methyl-2-pyridyl)ethoxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-methyl-2-pyridineethanol (97.2 g), p-fluorobenzonitrile (85.8 g) and dry tetrahydrofuran (600 ml) was added 60% sodium hydride in oil (29.0 g) in small portions with ice-cooling and stirring and the mixture was further stirred for 2 hours. The reaction mixture was poured in ice-water and extracted with ethyl ether. The ethyl ether layer was washed with water, dried (MgSO4) and concentrated, and the residue was crystallized from hexane to give 4-[2-(6-methyl-2-pyridyl)ethoxy]benzonitrile. Yield: 85.9 g (50.1%); m.p.: 66°-67° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hours
  3. extractionextracted with ethyl ether
  4. washThe ethyl ether layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-acf753d5931c41a088c9e9f901a015e2
Source dataset
uspto-grants-2000_02
Patent number
USRE036575

Linked notes

Loading…