Sodium hydride → HCID 54232873, compound

HRID 443048Notes

Reaction equation

HRID 443048 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:10]#[N:11])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].[Cl-].[NH4+]>CN(C)C=O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)([C:10]#[N:11])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 117544Ethyl 6-bromohexanoateHCID 234108bis(4-methoxyphenyl)acetonitrile

Product 1

HCID 54232873HCID 54232873, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of bis(4-methoxyphenyl)acetonitrile (1.0 g, 4 mmol) in N,N-dimethylformamide (5 ml) was added 60% oil sodium hydride (0.24 g, 6 mmol) while stirring under ice-cooling. The mixture was stirred for 30 minutes under the same conditions, to which was added, while stirring under ice-cooling, ethyl 6-bromohexanoate (0.89 g, 4 mmol). The mixture was stirred for 2 hours at room temperature, to which was added a saturated aqueous solution of ammonium chloride. The mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, which was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography, eluting with hexane--ethyl acetate (4:1) to give 1.1 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes under the same conditions, to which
  3. additionwas added
  4. stirringwhile stirring under ice-
  5. temperaturecooling
  6. stirringThe mixture was stirred for 2 hours at room temperature, to which
  7. extractionThe mixture was subjected to extraction with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materiala saturated aqueous saline solution, which was dried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. washeluting with hexane--ethyl acetate (4:1)

Sources & evidence

ORD record
ord-31aff8ee110b40c480187bee87bc892e
Source dataset
uspto-grants-1999_04
Patent number
US05891916

Reaction notes

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