Ethanol sodium ethoxide → HCID 58158583, compound

HRID 2095830Notes

Reaction equation

HRID 2095830 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][C:14](=O)[CH3:15])=[O:10])=[CH:4][CH:3]=1.[O-]CC.[Na+].C(O)C>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:10])[NH:11][CH2:12][CH2:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23706232Ethanol sodium ethoxideHCID 28347086HCID 28347086, compound

Product 1

HCID 58158583HCID 58158583, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-fluorophenyl)-N-(3-oxobutyl)acetamide (1.95 g, 8.7 mmol) in ethanol (120 mL) was added 20 wt % sodium ethoxide/ethanol solution (6.54 g, 19 mmol), and the mixture was stirred at 80° C. for 8 hr. The solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran and 1N aqueous hydrochloric acid solution were added to the residue, and the aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane (1/10) to give the title compound (1.36 g, 76%) as a brown solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, ethyl acetate/tetrahydrofuran and 1N aqueous hydrochloric acid solution
  2. additionwere added to the residue
  3. extractionthe aqueous layer was extracted with ethyl acetate/tetrahydrofuran (×3)
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe residue was washed with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-0cbf5576a30843628b7fec55c2d8c02b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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