Hydrochloric Acid → Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

HRID 1610172Notes

Reaction equation

HRID 1610172 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C(O)C.[H-].[Na+].Cl.[C:17](=O)([O:21]CC)[O:18][CH2:19][CH3:20]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH2:9][C:17]([O:18][CH2:19][CH3:20])=[O:21])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl CarbonateHCID 98284'-FluoroacetophenoneHCID 24758Sodium hydride

Product 1

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4′-fluoroacetophenone (57.8 g, 0.307 mol) and ethanol (1 ml) in diethyl carbonate (300 ml) was added sodium hydride (24.5 g, 60% in oil, 0.63 mol) by small portions. Because heat is gradually generated, the mixture was ice-cooled and stirred at room temperature for 2 hrs. To the reaction solution was added 6N hydrochloric acid to quench the reaction. Water (300 ml) was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1) to give ethyl 3-(4-fluorophenyl)-3-oxopropionate (71.2 g, 89%).

Workup

  1. temperatureBecause heat
  2. temperaturecooled
  3. customto quench
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-5:1)

Sources & evidence

ORD record
ord-f9f4427390b84e01b8fc5e18b066598f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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