Acetonitrile → 3-Cyclohexenylcarbonylacetonitrile

HRID 638646Notes

Reaction equation

HRID 638646 reaction equation
[H-].[Na+].[CH:3]1([C:9]([O:11]CC)=O)[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1.[C:14](#[N:16])[CH3:15]>C1(C)C=CC=CC=1>[CH:3]1([C:9]([CH2:15][C:14]#[N:16])=[O:11])[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 858033-Cyclohexene-1-carboxylic acid, ethyl ester

Product 1

HCID 135375663-CyclohexenylcarbonylacetonitrileYield 98.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

To a suspension of 1.25 g (2.60 mM) of 50% sodium hydride in 10 ml of toluene is added dropwise a solution of 2.01 g (1.30 mM) of ethyl 3-cyclohexenylcarboxylate 11 and 0.96 g (2.34 mM) of acetonitrile in 4 ml of toluene under nitrogen atmosphere in an hour and the mixture is stirred at 85° C. for 8 hours. After cooling, ice-cold water is added to the mixture. The aqueous phase is separated, washed with toluene, made acid with 10% hydrochloric acid and extracted with toluene. The extracted solution is washed with a dilute aqueous sodium hydrogencarbonate, and then with water, dried on magnesium sulfate and evaporated under reduced pressure. The resulting residue is chromatographed over silica gel and eluted with chloroform to give 1.91 g of the titled compound 8 as an yellow oil in 98.4% yield,

Workup

  1. temperatureAfter cooling
  2. additionice-cold water is added to the mixture
  3. customThe aqueous phase is separated
  4. washwashed with toluene
  5. extractionextracted with toluene
  6. washThe extracted solution is washed with a dilute aqueous sodium hydrogencarbonate
  7. dry with materialwith water, dried on magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe resulting residue is chromatographed over silica gel
  10. washeluted with chloroform

Sources & evidence

ORD record
ord-ae6faccf8e6a4ddd812766f993a6dc44
Source dataset
uspto-grants-1985_12
Patent number
US04562256

Reaction notes

Loading…