(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate → HCID 68748010, compound

HRID 333325Notes

Reaction equation

HRID 333325 reaction equation
[C:1](/[C:3](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]>CC(O)=O.C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Zn]>[C:1]([CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])#[N:2]

Participants

6

Reactant 1

HCID 68751356(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate

Product 1

HCID 68748010HCID 68748010, compoundYield 77.5%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (1.05 g, 3.52 mmol) and zinc (3.45 g, 52.8 mmol) in AcOH (20 ml) was allowed to stir at 100° C. After stirred for 1 hour, the reaction mixture was cooled to ambient temperature, and diluted with toluene and brine. The phases were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoate (819 mg); Retention time=1.41 minutes (condition B); MS (ES+)=317.0 (m+18).

Workup

  1. stirringAfter stirred for 1 hour
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customThe phases were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ac60e95d9b7405da0326c6a5336e5f7
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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