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

HRID 330293Notes

Reaction equation

HRID 330293 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH2:11][CH2:10][CH2:9]2.O>CS(C)=O>[CH2:11]1[C:12]2[C:8](=[CH:7][C:6]([CH2:5][C:1]#[N:2])=[CH:14][CH:13]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 2331495-(Chloromethyl)-2,3-dihydro-1h-indene

Product 1

HCID 148193682-(2,3-dihydro-1H-inden-5-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred, partial solution of NaCN (11.4 g, 0.232 mol) in DMSO 75 mL) was added 5-chloromethylindan (35.2 g, 0.211 mol) dropwise over 45 minutes. (The internal temperature was maintained below 65° C.). The resulting mixture was stirred at room temperature overnight. H2O (250 mL) was added and the mixture was extracted with ether. The organic phase was washed with H2O (200 mL), 6N HCl (100 mL), H2O (200 mL), saturated aqueous NaHCO3 (100 mL), and saturated aqueous NaCl, dried (MgSO4), and concentrated. The crude product was distilled under reduced pressure (0.6 mm) to give 28.1 g (85%) as a colorless oil, b.p. 131°) C.

Workup

  1. temperature(The internal temperature was maintained below 65° C.)
  2. extractionthe mixture was extracted with ether
  3. washThe organic phase was washed with H2O (200 mL), 6N HCl (100 mL), H2O (200 mL), saturated aqueous NaHCO3 (100 mL), and saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. distillationThe crude product was distilled under reduced pressure (0.6 mm)
  7. customto give 28.1 g (85%) as a colorless oil, b.p. 131°) C

Sources & evidence

ORD record
ord-3a50827db90644089c8ea36c068a65ed
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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