Sodium Cyanide → (1-Phenylcyclopentyl)acetonitrile

HRID 1409554Notes

Reaction equation

HRID 1409554 reaction equation
[C:1]1([C:7]2([CH2:12]OS(C)(=O)=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:18]#[N:19].[Na+]>CS(C)=O.O>[C:1]1([C:7]2([CH2:12][C:18]#[N:19])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 19437914(1-Phenylcyclopentyl)methyl methanesulfonate

Product 1

HCID 223258(1-Phenylcyclopentyl)acetonitrileYield 34.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (10 g, 39.37 mmol) in DMSO (30 ml) were added KI (0.6 g, 3.9 mmol) and NaCN (2.89 g, 59.05 mmol). It was then stirred at 140° C. for 16 h. After completion of the reaction, it was diluted with water, extracted with EtOAc and the organic layer was washed with water and brine. It was then dried over Na2SO4, concentrated and purified by normal column chromatography (15% EtOAc in hexanes) to afford the title compound as a colorless liquid (2.5 g, 34%).

Workup

  1. customAfter completion of the reaction, it
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with water and brine
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by normal column chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-573edee0a9e84a59a748ae79ecb4dd84
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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