Ethyl Acetate → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrile

HRID 1009394Notes

Reaction equation

HRID 1009394 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)[CH:9]=O.[C:20]([CH2:22]P(=O)(OCC)OCC)#[N:21].C(OCC)(=O)C>C1COCC1.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8](/[CH:9]=[CH:22]/[C:20]#[N:21])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 66839440(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrileYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A lithium hydroxide monohydrate powder (2.23 g) was added to a suspension of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (10 g) and diethyl cyanomethylphosphonate (8.2 g) in THF (50 ml) under ice-cooling, and the reaction solution was stirred at the same temperature for one hour. Ethyl acetate (200 mL) and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered through a silica gel pad (carrier: Chromatorex™ NH). The filtrate was concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate and hexane, and the crystals were collected by filtration. The resulting crystals were dried under reduced pressure to obtain 7.49 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered through a silica gel pad (carrier: Chromatorex™ NH)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was crystallized from ethyl acetate and hexane
  8. filtrationthe crystals were collected by filtration
  9. customThe resulting crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-87bab69f8ef54defa40bcf7de517d225
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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