Ethyl Acetate → HCID 58158561, compound

HRID 2095862Notes

Reaction equation

HRID 2095862 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([CH3:14])[CH:8]=1)=[O:5])#[N:2].CO/[CH:17]=[CH:18]/[C:19](=O)[CH3:20].N12CCN(CC1)CC2.C(OCC)(=O)C>COCCOCCO.O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])=[CH:8][C:9]=1[CH3:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9237DabcoHCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 17026974HCID 17026974, compound

Product 1

HCID 58158561HCID 58158561, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A solution (30 mL) of 2-cyano-N-(4-fluoro-3-methylphenyl)acetamide (3.60 g, 19.0 mmol), (3E)-4-methoxybut-3-en-2-one (2.80 g, 28.0 mmol) and 1,4-diazabicyclo[2.2.2]octane (3.20 g, 28.0 mmol) in 2-(2-methoxyethoxy)ethanol was stirred at 120° C. for 12 hr. After cooling to room temperature, the reaction solution was divided into two layers with ethyl acetate and water and subjected to extraction (3 times) with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (1.60 g, 34%) as a brown solid.

Workup

  1. extractionsubjected to extraction (3 times) with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe obtained residue was washed with ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d32a1472fd09436c95dd9ce4eabea039
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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