Sodium Cyanide → 2-(6-Methoxyindan-1-yl)acetonitrile

HRID 2165154Notes

Reaction equation

HRID 2165154 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12]OS(C)(=O)=O)=[CH:5][CH:4]=1.[C-:18]#[N:19].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:18]#[N:19])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 17883324Methanesulphonic acid (6-methoxyindan-1-ylmethyl) ester

Product 1

HCID 130459302-(6-Methoxyindan-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

12.8 g (50 mmol) of methanesulphonic acid (6-methoxyindan-1-ylmethyl) ester and 3.7 g (75 mmol) of sodium cyanide are dissolved in 70 ml of dimethyl sulphoxide and heated at 80° for 6 hours. The reaction mixture is poured onto 200 ml of ice-water and extracted three times by shaking with 100 ml of toluene each time. The organic phases are combined, subsequently washed with saturated sodium chloride solution and dried over magnesium sulphate. After removing the solvent in vacuo, crude 2-(6-methoxyindan-1-yl)acetonitrile is obtained.

Workup

  1. temperatureheated at 80° for 6 hours
  2. extractionextracted three times
  3. washsubsequently washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customAfter removing the solvent in vacuo

Sources & evidence

ORD record
ord-a952fad7214e4c9c80c6de6fb950f446
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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