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

HRID 1978911Notes

Reaction equation

HRID 1978911 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 in 100 ml of isopropanol with 5.7 g (35 mmol) of 2-methoxyethyl acetoacetate. 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 to this solution and it is stirred overnight at 40° C. The mixture is concentrated, the residue is taken up in toluene, the solution is concentrated again and the residue is purified by filtration on 100 ml of silica gel (eluent: 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. concentrationthe solution is concentrated again
  3. filtrationthe residue is purified by filtration on 100 ml of silica gel (eluent: toluene/ethyl acetate 100:1)

Sources & evidence

ORD record
ord-d4566fd42219427c836955083273fab3
Source dataset
uspto-grants-2001_05
Patent number
US06239155B1

Reaction notes

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