Cyclohexanone → Acetonitrile, cyclohexylidene-

HRID 1167888Notes

Reaction equation

HRID 1167888 reaction equation
[H-].[Na+].P(=O)([O-])O[C:5](CC)(CC)[C:6]#[N:7].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCCC1>[C:14]1(=[CH:5][C:6]#[N:7])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 24758Sodium hydrideHCID 178449162HCID 178449162, compound

Product 1

HCID 97105Acetonitrile, cyclohexylidene-Yield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium hydride (60% in oil, 0.80 g, 20 mmol) was suspended in 50 mL tetrahydrofuran and chilled in ice under nitrogen. Diethylcyanomethyl phosphonate (3.85 g, 22 mmol) was added dropwise in 10 mL tetrahydrofuran and stirring continued for 15 minutes to give a clear solution. Cyclohexanone (1.90 g, 19 mmol) was added in 5 mL tetrahydrofuran and the reaction mixture allowed to warm up to room temperature. The liquor was decanted and the residue washed three times with ether. The liquor and washings were combined, washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1 to give the required product as a colorless oil (1.5 g, 67%).

Workup

  1. temperaturechilled in ice under nitrogen
  2. customto give a clear solution
  3. customThe liquor was decanted
  4. washthe residue washed three times with ether
  5. washwashed with dilute hydrochloric acid and water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-aa4aa6e2c954416093a6cff733a25240
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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