Ethyl Acetate → HCID 20083372, compound

HRID 1609130Notes

Reaction equation

HRID 1609130 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]#[N:27])=[CH:16][CH:15]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])=[CH:18][CH:19]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 836092,6-Dimethylpyridin-4(1H)-oneHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 20083372HCID 20083372, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

369 mg of 2,6-dimethyl-4(1H)-pyridone was dissolved in 5 ml of N,N-dimethylformamide. To this solution was added 144 mg of 60% sodium hydride, followed by stirring at room temperature for 15 minutes. Subsequently, 900 mg of 4-bromomethyl-2'-cyanobiphenyl was added to the mixture, and the mixture was stirred at room temperature for two hours. After the reaction was completed, ethyl acetate was added to the reaction mixture, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, to which was added ethyl acetate. The precipitated crystals were collected by filtration and then dried, and, on the other hand, the filtrate was purified by a silica gel column chromatography (80 g, chloroform:ethyl acetate=3:1 to 2:3), whereby 296 mg and 329 mg of 2,6-dimethyl-4-(2'-cyanobiphenyl-4-yl)methoxypyridine were obtained, respectively (total amount: 625 mg, yield: 66%).

Workup

  1. stirringthe mixture was stirred at room temperature for two hours
  2. washthe mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure, to which
  5. additionwas added ethyl acetate
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried
  8. customon the other hand, the filtrate was purified by a silica gel column chromatography (80 g, chloroform:ethyl acetate=3:1 to 2:3), whereby 296 mg

Sources & evidence

ORD record
ord-595c2b5807dd48f5901487e0b7447392
Source dataset
uspto-grants-1995_03
Patent number
US05399566

Reaction notes

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