Acetonitrile → 2,3-Dihydro-1H-indene-2-carbonitrile

HRID 450727

Reaction equation

HRID 450727 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1OS(C)(=O)=O.[C:15](#[N:17])C>[C-]#N.C([N+](CC)(CC)CC)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:15]#[N:17]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonate

Product 1

HCID 232396182,3-Dihydro-1H-indene-2-carbonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Conditions

Temperature
55 °C

Procedure

A mixture of methanesulfonic acid indan-2-yl ester (18.65 g, 87.9 mmol) and tetraethylammonium cyanide (15.10 g) in acetonitrile (180 mL) was heated to 55° C. for 5 hours, cooled and concentrated. The residue was partitioned between ethyl acetate and water, and the organic phase separated. This was dried over MgSO4 and the filtered solution was concentrated and then separated by column chromatography (dichloromethane:ethyl acetate, 6:1-1:1) to give the product as a red solid (6.51 g, 52%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organic phase separated
  5. dry with materialThis was dried over MgSO4
  6. concentrationthe filtered solution was concentrated
  7. customseparated by column chromatography (dichloromethane:ethyl acetate, 6:1-1:1)

Sources & evidence

ORD record
ord-b09be4f86e70459ba16dd2d42dc4a312
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Linked notes

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