2-Nitropropane → Ethyl 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylate

HRID 2240844Notes

Reaction equation

HRID 2240844 reaction equation
[CH2:1]([O:3][C:4](=[O:15])/[C:5](/[C:13]#[N:14])=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[N+]([CH:19]([CH3:21])[CH3:20])([O-])=O.C(=O)([O-])[O-].[K+].[K+].[Na+].[Cl-]>CCO>[CH2:1]([O:3][C:4]([C:5]1([C:13]#[N:14])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:19]1([CH3:21])[CH3:20])=[O:15])[CH3:2]

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 668187alpha-Cyanocinnamic acid ethyl ester

Product 1

HCID 13429895Ethyl 1-Cyano-2,2-dimethyl-3-phenylcyclopropanecarboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester (83.6 g, 415 mmol), 2-nitropropane (37 g, 415 mmol) and potassium carbonate (57.4 g, 415 mmol) in EtOH (325 mL) was heated at reflux for 4 hours, then heated to 50° C. for 18 hours. The reaction mixture was then poured into an aqueous solution of NaCl (15%, 2 L) and extracted with DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by distillation under vacuum to give 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid ethyl ester (64.26 g, 64% yield, pale yellow oil) which distilled at 118° C. (oil bath temperature 157° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. distillationThe residue was purified by distillation under vacuum

Sources & evidence

ORD record
ord-db4c3d65632b4de791e0c86a26a5b854
Source dataset
uspto-grants-2010_05
Patent number
US07723391B2

Reaction notes

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