Acetic Acid → Ethyl 2-cyano-2-cyclopropylacetate

HRID 714812

Reaction equation

HRID 714812 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH:11]1([CH2:14][C:15]#[N:16])[CH2:13][CH2:12]1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:15]([CH:14]([CH:11]1[CH2:13][CH2:12]1)[C:3]([O:7][CH2:8][CH3:9])=[O:10])#[N:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 643447Cyclopropylacetonitrile

Product 1

HCID 10606956Ethyl 2-cyano-2-cyclopropylacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of sodium hydride (60% in mineral oil, 38 g) and diethyl carbonate (97 mL) in toluene (240 mL) was added dropwise a solution of cyclopropylacetonitrile (32 g) in toluene (120 mL) over 40 min with heating under reflux, and the mixture was heated under reflux for additional 2 hr. The mixture was neutralized with acetic acid (120 mL) in an ice bath, water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was distilled (boiling point 69-72° C., 4.0 mmHg) to give the title compound (50 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for additional 2 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. distillationThe residue was distilled (boiling point 69-72° C., 4.0 mmHg)

Sources & evidence

ORD record
ord-a8056b8feeef4ce19a2335a9680a46aa
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Linked notes

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