Acetic Acid → 2-Methoxyethyl 2-acetyl-3-(2-fluorophenyl)-2-propenoate

HRID 1978910Notes

Reaction equation

HRID 1978910 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([O:16][CH2:17][CH2:18][O:19][CH3:20])(=[O:15])[CH2:11][C:12]([CH3:14])=[O:13].N1CCCCC1.C(O)(=O)C>C(O)(C)C>[C:12]([C:11](=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])[C:10]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[O:15])(=[O:13])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 67970o-FluorobenzaldehydeHCID 897342-Methoxyethyl acetoacetate

Product 1

HCID 599577782-Methoxyethyl 2-acetyl-3-(2-fluorophenyl)-2-propenoateYield 70.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
40 °C

Procedure

10 g (80 mmol) of 2-fluorobenzaldehyde are dissolved in 200 ml of isopropanol with 13 g (80 mmol) of 2-methoxyethyl acetoacetate. A freshly prepared solution of 1.0 ml of piperidine and 0.5 ml of glacial acetic acid in 10 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 300 ml of silica gel (eluent: toluene/ethyl acetate 100:1-10:1) to give 15 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 300 ml of silica gel (eluent: toluene/ethyl acetate 100:1-10:1)

Sources & evidence

ORD record
ord-500767d147a74da18ec28545b3055d27
Source dataset
uspto-grants-2001_05
Patent number
US06239155B1

Reaction notes

Loading…