Sodium hydride → 6-[(2',6'-Dimethylbiphenyl-3-yl)methoxy]nicotinonitrile

HRID 2426758Notes

Reaction equation

HRID 2426758 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1.Cl[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=1>C1COCC1>[CH3:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH3:3])[C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][N:21]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 230827203-(2,6-Dimethylphenyl)benzyl alcohol

Product 1

HCID 577873276-[(2',6'-Dimethylbiphenyl-3-yl)methoxy]nicotinonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, sodium hydride was added under ice-cooling to a THF solution of (2′,6′-dimethylbiphenyl-3-yl)methanol, followed by stirring at that temperature for 15 minutes. Thereafter, 6-chloronicotinonitrile was added to the reaction mixture under ice-cooling, followed by warming up to room temperature and stirring for 3 hours to obtain 6-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]nicotinonitrile.

Workup

  1. temperaturecooling
  2. stirringstirring for 3 hours

Sources & evidence

ORD record
ord-65f5403e68a94489bc5e8390a4106945
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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