Hydrochloric Acid → Acetonitrile, 2-(2,4,4-trimethylcyclopentylidene)-

HRID 2045760Notes

Reaction equation

HRID 2045760 reaction equation
C(OP([CH2:9][C:10]#[N:11])(OCC)=O)C.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].[C:17]1(=O)[CH2:21][CH2:20]CC1.Cl.O1CCC[CH2:25]1>CCCCCC>[CH3:15][CH:14]1[CH2:25][C:21]([CH3:20])([CH3:17])[CH2:12][C:13]1=[CH:9][C:10]#[N:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8452CyclopentanoneHCID 75676Diethyl (cyanomethyl)phosphonateHCID 178418339Butyllithium

Product 1

HCID 67064889Acetonitrile, 2-(2,4,4-trimethylcyclopentylidene)-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

1.1 eq. of diethylphosphonoacetonitrile are placed in THF (tetrahydrofuran) under an inert atmosphere. 1.1 eq. of a solution of butyllithium in hexane are added thereto dropwise at approximately 10° C. The mixture is subsequently stirred at ambient temperature for one hour before adding, dropwise, 1 eq. of cyclopentanone A at approximately 10° C. The reaction medium is stirred at ambient temperature for a few hours and is then poured onto a 10% HCl solution. The aqueous phase is extracted three times with MTBE. The combined organic phases are washed with a sodium bicarbonate solution and then with an aqueous sodium chloride solution. After drying over magnesium sulfate, filtering through paper and evaporating the solvent, the crude product is distilled under reduced pressure. A 75:25 mixture of the trans and cis isomers of 2-(2,4,4-trimethyl-cyclopentylidene) acetonitrile is obtained.

Workup

  1. customdropwise at approximately 10° C
  2. additionbefore adding
  3. customat approximately 10° C
  4. stirringThe reaction medium is stirred at ambient temperature for a few hours
  5. extractionThe aqueous phase is extracted three times with MTBE
  6. washThe combined organic phases are washed with a sodium bicarbonate solution
  7. dry with materialAfter drying over magnesium sulfate
  8. filtrationfiltering through paper
  9. customevaporating the solvent
  10. distillationthe crude product is distilled under reduced pressure
  11. additionA 75:25 mixture of the trans
  12. customis obtained

Sources & evidence

ORD record
ord-9f259d3439b74e2681bd01192d524c90
Source dataset
uspto-grants-2013_11
Patent number
US08592360B2

Reaction notes

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