Acetic Acid → 3-(3,5-Dichlorophenyl)-2-propionyl-acrylic methylester

HRID 1182576Notes

Reaction equation

HRID 1182576 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5](=[O:8])[CH2:6][CH3:7].[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[CH:14]=O.N1CCCCC1.C(O)(=O)C>CC(O)C>[CH3:1][O:2][C:3](=[O:9])[C:4]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:14][C:13]1[CH:12]=[C:11]([Cl:10])[CH:18]=[C:17]([Cl:19])[CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 357463,5-DichlorobenzaldehydeHCID 121699Methyl 3-oxovalerate

Product 1

HCID 858136683-(3,5-Dichlorophenyl)-2-propionyl-acrylic methylester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.00 g (7.68 mmol) of 3-oxovaleric acid methylester and 1.34 g (7.68 mmol) of 3,5-dichlorobenzaldehyde were dissolved in 20 ml of 2-propanol. 65.4 mg (0.768 mmol) of piperidine and 46.1 mg (0.768 mmol) of acetic acid were added and stirred at room temperature for one day. After the solvent was evaporated under reduced pressure, ethyl acetate was added thereto. The reaction mixture was washed with 1 N hydrochloric acid and then with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1) to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washThe reaction mixture was washed with 1 N hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-a5f305178f3e4e459070de8507c39122
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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