Water → HCID 22262275, compound

HRID 1610311Notes

Reaction equation

HRID 1610311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1.O>COCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5209941-(Chloromethyl)-4-phenoxybenzeneHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 22262275HCID 22262275, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of ethyl 3-(4-fluorophenyl)-3-oxopropionate (6.49 g, 30.9 mmol) in 1,2-dimethoxyethane (50 ml) was added sodium hydride (60% in oil, 1.23 g, 30.9 mmol) under ice-cooling and the mixture was stirred at room temperature for 30 min. To the reaction solution was dropwise added a solution of 1-(chloromethyl)-4-(phenyloxy)benzene (8.1 g, 37.0 mmol) in 1,2-dimethoxyethane (50 ml) and the reaction solution was heated under reflux overnight. The reaction solution was poured into water (200 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:hexane=1:1-toluene) to give ethyl 3-(4-fluorophenyl)-3-oxo-2-((4-(phenyloxy)phenyl)methyl)propionate (7.76 g, crude, 64%).

Workup

  1. temperaturecooling
  2. temperaturethe reaction solution was heated
  3. temperatureunder reflux overnight
  4. extractionextracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (toluene:hexane=1:1-toluene)

Sources & evidence

ORD record
ord-758f8dccefcf4bd4acade71c84a20c8d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…