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

HRID 1727899Notes

Reaction equation

HRID 1727899 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-3cb7f186df88405399f8c55e3100b39f
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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