Hydrochloric Acid → 3-Cyclohexyl-3-oxopropanenitrile

HRID 2224649Notes

Reaction equation

HRID 2224649 reaction equation
[NH2-].[Na+].[C:3](#[N:5])[CH3:4].[CH:6]1([C:12](OC)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Cl>O1CCCC1>[CH:6]1([C:12](=[O:13])[CH2:4][C:3]#[N:5])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 20748Methyl cyclohexanecarboxylateHCID 24533Sodium amide

Product 1

HCID 113095973-Cyclohexyl-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of sodium amide (1.87 g) in tetrahydrofuran (10 ml) was added acetonitrile (2.72 ml) dropwise at −50-−40° C. and then thereto was added cyclohexane carboxylic acid, methyl ester (2.86 ml) and the mixture was stirred for 1 hour at −20° C. The reaction mixture was poured into cold hydrochloric acid and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (0.91 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7c1e6f67bd7241ef95db985e607acd1c
Source dataset
uspto-grants-2008_05
Patent number
US07378428B2

Reaction notes

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