Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

HRID 1497240Notes

Reaction equation

HRID 1497240 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.Cl>[CH:3]1([C:8](=[O:10])[CH2:13][C:12]#[N:14])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylate

Product 1

HCID 135921183-Cyclopentyl-3-oxopropanenitrileYield 77%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (1.87 g, 55% in mineral oil, 42.9 mmol) in THF (10 ml) was added a solution of methyl cyclopentanecarboxylate (5 g, 39.0 mmol) and acetonitrile (1.92 g, 2.45 ml, 46.8 mmol) in THF (3 ml) dropwise at 70° C. The mixture was heated to 70° C. overnight, then cooled to room temperature, diluted with 1N HCl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5-85:15) to afford the title compound (4105 mg, 77%) as light yellow liquid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5-85:15)

Sources & evidence

ORD record
ord-0891bfe621234244a797c972ab8d2e7a
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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