Ethyl Acetate → 1-(3-Chlorophenyl)butane-1,3-dione

HRID 1466591Notes

Reaction equation

HRID 1466591 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[CH:5]=1)=[O:3].[CH3:11][C:12](C)([O-:14])C.[K+].C(OCC)(=O)C>C1COCC1>[Cl:10][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH2:1][C:12](=[O:14])[CH3:11])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 149331-(3-Chlorophenyl)ethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 152569661-(3-Chlorophenyl)butane-1,3-dioneYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-chloroacetophenone (1.30 mL, 10.0 mmol) in 20 mL THF was added Potassium tert-butoxide (11.0 mL of a 1.0 M solution in THF, 11.0 mmol) and then anhydrous ethyl acetate (1.05 mL, 10.7 mmol). The reaction was stirred at room temperature for 2 hours and then at 50° C. for 15 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic portion washed with brine, dried over magnesium sulfate, and concentrated. The crude product was purified by flash chromatography on silica gel (0 to 50% ethyl acetate in heptanes) to yield 0.75 g (38%) of 1-(3-chlorophenyl)butane-1,3-dione. LCMS (ESI) m+H=197.2.

Workup

  1. waitat 50° C. for 15 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe organic portion washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (0 to 50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-f6d0f7b9ae694021bdd57880fd251308
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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