Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

HRID 2169148Notes

Reaction equation

HRID 2169148 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16]Br.CCOCC>CS(C)=O>[C:3]1([C:9]2([C:10]#[N:11])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 661681-Phenylcyclopentanecarbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of sodium hydride (60%, 18.8 g, 470.08 mmol) in dimethyl sulfoxide (125 mL) was added dropwise a mixture of phenyl acetonitrile (19-01) (25 g, 213.6 mmol) and 1,4-dibromo-butane (20) (25.5 mL, 213.67 mmol) dissolved in dimethyl sulfoxide:ether (300 mL, 1:1). The mixture was stirred at room temperature for 3 h. After completion of the reaction, it was quenched with 1N HCl. The mixture was extracted with ethyl acetate, the separated organic part was dried and concentrated to get a crude product which was purified using normal silica column using 3% ethyl acetate in hexane to of ford 1-phenyl-cyclopentanecarbonitrile (21-01) (34 g, 92.92%) as a yellow liquid.

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction, it
  3. customwas quenched with 1N HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe separated organic part was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d500b1f6f08b4da2b2aaef445fe96e7d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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