Acetonitrile → 3-(2-Methylcyclopropyl)-3-oxopropanenitrile

HRID 1943910Notes

Reaction equation

HRID 1943910 reaction equation
[C:1](#[N:3])[CH3:2].CC(C)(C)C[O-].[K+].C([O:13][C:14]([CH:16]1[CH2:18][CH:17]1[CH3:19])=O)C>C1COCC1>[CH3:19][CH:17]1[CH2:18][CH:16]1[C:14](=[O:13])[CH2:2][C:1]#[N:3]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 89405Ethyl 2-methylcyclopropanecarboxylateHCID 23675521Potassium 2,2-dimethylpropan-1-olate

Product 1

HCID 431156733-(2-Methylcyclopropyl)-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetonitrile (0.102 mL, 1.95 mmol) was dissolved in THF. Potassium 2,2-dimethylpropan-1-olate (3.44 mL, 5.85 mmol) was added, followed by addition of ethyl-2-methylcyclopropanecarboxylate (1.0 g, 7.80 mmol). After five minutes, the reaction mixture was quenched with 1N HCl and then partitioned with EtOAc. The organic layer was washed with water (3×), brine, dried over Na2SO4 and concentrated to give 3-(2-methylcyclopropyl)-3-oxopropanenitrile as an oil, which was used in the next step without further purification.

Workup

  1. customthe reaction mixture was quenched with 1N HCl
  2. custompartitioned with EtOAc
  3. washThe organic layer was washed with water (3×), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cddf1b2ef8ff487eaa7b4c61292d63a7
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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