Diphenylacetonitrile → HCID 19028748, compound

HRID 2256330Notes

Reaction equation

HRID 2256330 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>O1CCCC1.O>[C:8]([C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:9]

Participants

6

Reactant 3

HCID 6837DiphenylacetonitrileHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Product 1

HCID 19028748HCID 19028748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diphenylacetonitrile (1 g) in tetrahydrofuran (10 ml) was added 60% sodium hydride (0.25 g) portionwise under ice-cooling and stirring. After completion of portionwise addition, the mixture was further stirred for 15 minutes. Then, ethyl bromoacetate (0.69 ml) was added dropwise and the mixture was further stirred for 30 minutes. The reaction mixture was then diluted with water and the organic layer was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to provide the title compound (1.2 g) as colorless powder.

Workup

  1. temperaturecooling
  2. additionAfter completion of portionwise addition
  3. stirringthe mixture was further stirred for 15 minutes
  4. stirringthe mixture was further stirred for 30 minutes
  5. extractionthe organic layer was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-112cda80e6e54277b8a33124432f5aa2
Source dataset
uspto-grants-1997_08
Patent number
US05654296

Reaction notes

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