Acetic Acid → 2-Methoxyethyl 2-acetyl-3-(2,4-difluorophenyl)-2-propenoate

HRID 1108293Notes

Reaction equation

HRID 1108293 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH2:18][CH2:19][O:20][CH3:21])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].N1CCCCC1.C(O)(=O)C>C(O)(C)C>[C:13]([C:12](=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1])[C:11]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[O:16])(=[O:14])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 737702,4-DifluorobenzaldehydeHCID 897342-Methoxyethyl acetoacetate

Product 1

HCID 543348912-Methoxyethyl 2-acetyl-3-(2,4-difluorophenyl)-2-propenoateYield 50.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
40 °C

Procedure

5.0 g (35 mmol) of 2,4-difluorobenzaldehyde are dissolved with 5.7 g (35 mmol) of 2-methoxyethyl acetoacetate in 100 ml of isopropanol. A freshly prepared solution of 1.0 ml of piperidine and 0.5 ml of glacial acetic acid in 5 ml of isopropanol is added and the mixture is stirred at 40° C. overnight. The mixture is concentrated, the residue is taken up in toluene, this mixture is concentrated again and the residue is purified by filtration over 100 ml of silica gel (mobile phase: toluene/ethyl acetate 100:1) to give 5 g of the target compound as a yellow oil, which is immediately reacted further.

Workup

  1. concentrationThe mixture is concentrated
  2. concentrationthis mixture is concentrated again
  3. filtrationthe residue is purified by filtration over 100 ml of silica gel (mobile phase: toluene/ethyl acetate 100:1)

Sources & evidence

ORD record
ord-11715cf96a464a69b66f8ba7c63fe767
Source dataset
uspto-grants-2000_05
Patent number
US06066655

Reaction notes

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