Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

HRID 1930357Notes

Reaction equation

HRID 1930357 reaction equation
[CH:1]1([C:6]([O:8]CC)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:11](#[N:13])[CH3:12].[H-].[Na+]>C1COCC1>[CH:1]1([C:6](=[O:8])[CH2:12][C:11]#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 79550Ethyl cyclopentanecarboxylate

Product 1

HCID 135921183-Cyclopentyl-3-oxopropanenitrileYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl cyclopentanecarboxylate (prepared by esterification of commercially available cyclopentantecarboxylic acid, 30 g, 0.21 mol) and acetonitrile (10.1 g, 0.25 mol) in dry THF (80 mL) was added dropwise to a suspension of NaH (12.5 g, 0.31 mol) in dry THF (80 mL) and the resulting mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure and partitioned between water and EtOAc. The aqueous layer was separated, adjusted to pH 8 and extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), and concentrated to give 3-cyclopentyl-3-oxopropanenitrile (26 g, 90% yield), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ4.06 (s, 2 H), 2.92 (m, 1 H), 1.41-1.77 (m, 8 H).

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between water and EtOAc
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-abee91d8f9b244a181ee4a5366552510
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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