Sodium Cyanide → 2-(2,3-dihydro-1H-inden-5-yl)acetonitrile

HRID 468500Notes

Reaction equation

HRID 468500 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH2:7][CH2:6]2.[C-:12]#[N:13].[Na+]>CS(C)=O>[CH2:8]1[C:9]2[C:5](=[CH:4][C:3]([CH2:2][C:12]#[N:13])=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indene

Product 1

HCID 148193682-(2,3-dihydro-1H-inden-5-yl)acetonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 5-(chloromethyl)-2,3-dihydro-1H-indene (90.0 g, 0.54 mol) in DMSO (500 ml) was added sodium cyanide (54.0 g, 1.08 mol) at 0° C. portion wise. The reaction mixture was then stirred at room temperature for 3 hours. The reaction was quenched with water (1000 ml), extracted with ethyl acetate (3×250 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated in vacuo to afford 2-(2,3-dihydro-1H-inden-5-yl)acetonitrile (82.2 g, 97%), that was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with water (1000 ml)
  2. extractionextracted with ethyl acetate (3×250 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-da7194fa1ad14a718058da438e643759
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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