Bromoacetonitrile → HCID 19045725, compound

HRID 1781492Notes

Reaction equation

HRID 1781492 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:19][C:20]#[N:21]>O1CCCC1>[C:10]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH:8]=[O:9])[CH2:19][C:20]#[N:21])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 13696DiphenylacetaldehydeHCID 24758Sodium hydride

Product 1

HCID 19045725HCID 19045725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diphenylacetoaldehyde (1 g) in tetrahydrofuran (10 ml) was added a suspension of 60% sodium hydride (0.25 g) in tetrahydrofuran (5 ml) carefully dropwise under ice-cooling and stirring. After completion of dropwise addition, the mixture was further stirred for 20 minutes. Then, bromoacetonitrile (0.41 ml) was added and the mixture was further stirred for 30 minutes. The reaction mixture was poured in ice-water and the oil that had separated out was extracted into ethyl acetate. The organic layer was taken, washed with water, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was purified by silica gel column chromatography to provide the title compound (0.85 g) as colorless oil.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. stirringthe mixture was further stirred for 20 minutes
  4. stirringthe mixture was further stirred for 30 minutes
  5. customthe oil that had separated out
  6. extractionwas extracted into ethyl acetate
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe group was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a967e5e88454d92891b438873ad9c10
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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