Diphenylacetonitrile → Ethyl 5-cyano-5,5-diphenylpentanoate

HRID 1781497Notes

Reaction equation

HRID 1781497 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][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O1CCCC1>[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][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])#[N:9]

Participants

5

Reactant 3

HCID 6837DiphenylacetonitrileHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 19028947Ethyl 5-cyano-5,5-diphenylpentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of diphenylacetonitrile (1-g) in tetrahydrofuran (10 ml) was added 60% sodium hydride (0.25 g) in small portions under ice-cooling. After completion of dropwise addition, the mixture was stirred for 20 minutes. Then, ethyl 4-bromobutyrate (0.94 ml) was added dropwise under ice-cooling and the mixture was further stirred at room temperature for 15 minutes. This reaction mixture was poured into ice-water and the organic layer that had separated out was extracted with ethyl acetate. The extract was 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 (0.87 g) as colorless oil.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. temperaturecooling
  4. stirringthe mixture was further stirred at room temperature for 15 minutes
  5. customthe organic layer that had separated out
  6. extractionwas extracted with ethyl acetate
  7. washThe extract was washed 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-93d6f4d190a449699491ef1331779bbf
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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