Hydrochloric Acid → 3-Cyclohexyl-3-oxopropanenitrile

HRID 967760Notes

Reaction equation

HRID 967760 reaction equation
[NH2-].[Na+].[C:3](#[N:5])[CH3:4].C[O:7][C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=O.Cl>O1CCCC1>[CH:10]1([C:8](=[O:7])[CH2:4][C:3]#[N:5])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]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 (1.87 g) was added acetonitrile (2.72 ml) at −50˜−40° C. dropwise and then was added cyclohexanecarboxylic acid methyl ester (2.86 ml) and the mixture was stirred for 1 hour at −20° C. The reaction mixture was poured into cool hydrochloric acid and was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride successively, and was dried over anhydrous magnesium sulfate and then 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. additionThe reaction mixture was poured
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride successively, and was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8072c4621a9c4dcc8965a6ae5aceec43
Source dataset
uspto-grants-2005_10
Patent number
US06956033B2

Reaction notes

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