Acetonitrile → 3-Cyclohexyl-3-oxopropanenitrile

HRID 1241599Notes

Reaction equation

HRID 1241599 reaction equation
C([Li])CCC.[CH3:6][C:7]#[N:8].[CH:9]1([C:15](OC)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1COCC1>[CH:9]1([C:15](=[O:16])[CH2:6][C:7]#[N:8])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 20748Methyl cyclohexanecarboxylateHCID 178418339Butyllithium

Product 1

HCID 113095973-Cyclohexyl-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 700 mL of THF cooled at −78° C. under inert atmosphere was added n-butyllithium (56 mL, 2.5 M in hexane) followed by CH3CN (7.3 mL, 0.14 mol) maintaining the temperature below −70° C. The mixture was stirred at −78° C. for 20 min then a solution of methyl cyclohexane carboxylate (10 g, 0.07 mol) in dry THF (300 mL) was added dropwise, maintaining the temperature under −60° C. The reaction was stirred an additional 20 min at −78° C., warmed to −20° C. and quenched by addition of saturated aq. NH4Cl. The reaction mixture was diluted with H2O and extracted with t-BuOMe. The solvents were removed under vacuum to give 3-cyclohexyl-3-oxopropanenitrile as a colorless oil.

Workup

  1. temperaturemaintaining the temperature below −70° C
  2. temperaturemaintaining the temperature under −60° C
  3. stirringThe reaction was stirred an additional 20 min at −78° C.
  4. temperaturewarmed to −20° C.
  5. customquenched by addition of saturated aq. NH4Cl
  6. additionThe reaction mixture was diluted with H2O
  7. extractionextracted with t-BuOMe
  8. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-58515693220143618fe08d3d6f947c0e
Source dataset
uspto-grants-2006_10
Patent number
US07115617B2

Reaction notes

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