Hydrochloric Acid → 1-Phenylcyclopentanecarbonitrile

HRID 1409551Notes

Reaction equation

HRID 1409551 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.Cl>CS(C)=O.O.CCOCC>[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 661681-PhenylcyclopentanecarbonitrileYield 86.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of NaH (11.3 g, 281.7 mmol, 60%) in DMSO (75 ml) were added dropwise a mixture of phenyl-acetonitrile (15 g, 128.0 mmol) and 1,4-dibromo-butane (18 ml, 128.0 mmol) dissolved in DMSO:Ether (150 ml, 1:1) at 0° C. and the reaction mixture was stirred at room temperature (RT) for 2 to 3 h. After completion of the reaction, water and 10% HCl solution were added to the crude mass. It was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (10% EtOAc-hexane) to get 1-phenyl-cyclopentanecarbonitrile (2) (19 g, 86.64%) as a yellow solid. MS: m/z=171 (MH+).

Workup

  1. additionwere added dropwise
  2. additionwere added to the crude mass
  3. extractionIt was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (10% EtOAc-hexane)

Sources & evidence

ORD record
ord-b4203385e32e47fda13e193367799b70
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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