Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

HRID 915556Notes

Reaction equation

HRID 915556 reaction equation
[H-].[Na+].[CH:3]1([C:8]([O:10]C)=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:12](#[N:14])[CH3:13]>C1COCC1.C(OCC)(=O)C.Cl>[CH:3]1([C:8](=[O:10])[CH2:13][C:12]#[N:14])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylate

Product 1

HCID 135921183-Cyclopentyl-3-oxopropanenitrile

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (2.75 g, 68.7 mmol) in THF (15 mL) at 70° C. was added dropwise a solution of methyl cyclopentanecarboxylate (8.00 g, 62.4 mmol) and anhydrous acetonitrile (3.91 mL, 74.9 mmol) in THF (5 mL). The mixture was stirred for 16 h at 70° C.-72° C., cooled to rt, and diluted with ethyl acetate and aqueous HCl. The organic layer was washed with water and brine and dried (MgSO4). Removal of the solvent provided 3-cyclopentyl-3-oxopropanenitrile, which was used without further purification.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-cf2751e4567d4b2d9b7f3ce6d3611c27
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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