Water → HCID 19097808, compound

HRID 486298Notes

Reaction equation

HRID 486298 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([N:9]([CH2:20][C:21](=O)[CH2:22][CH3:23])[C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[O-]CC.[Na+].O>C(O)C>[CH2:22]([C:21]1[CH2:20][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:26])([F:25])[F:1])[CH:4]=2)[C:10](=[O:19])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 2723922Sodium ethoxideHCID 19097810HCID 19097810, compound

Product 1

HCID 19097808HCID 19097808, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2.74 g (7.47 mmol) of N-(3-trifluoromethylphenyl)-N-(2-oxobutyl)-3-fluorophenylacetamide synthesized in the same manner as in Example 3 were dissolved in 30 ml of ethanol, and 0.05 ml of an ethanol solution containing 30% of sodium ethoxide was added thereto at room temperature with stirring. The solution was stirred at the same temperature for 2 hours, and the resultant reaction mixture was then poured into water, followed by extraction with ethyl acetate. Afterward, the resultant organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The precipitated crystals were collected by filtration, and then washed with diethyl ether to obtain 2.15 g of the desired product in the state of colorless crystals (yield 82.4%).

Workup

  1. additionwas added
  2. stirringThe solution was stirred at the same temperature for 2 hours
  3. customthe resultant reaction mixture
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialAfterward, the resultant organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-5e9e2b44326a49c1a0a3cced1de09847
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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