Methyl 4-methoxyacetoacetate → HCID 54115946, compound

HRID 565220Notes

Reaction equation

HRID 565220 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[F:20])[CH:15]=O.C([O-])(=O)C.[NH2+]1CCCCC1>C1C=CC=CC=1>[F:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:5]([C:4](=[O:10])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH3:9])=[O:7])[CH:17]=[CH:18][C:19]=1[F:20]

Participants

5

Reactant 3

HCID 123500Methyl 4-methoxyacetoacetateHCID 5880883,4-DifluorobenzaldehydeHCID 3014295Piperidinium acetate

Product 1

HCID 54115946HCID 54115946, compoundYield 42,970.199%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl 4-methoxyacetoacetate (84.32 g, 0.577 mol), 3,4-difluorobenzaldehyde (82 g, 0.577 mmol), and piperidinium acetate (5.86 g, 0.068 mol) in benzene (1.5 L) were added molecular sieves (400 g) and the mixture was stirred at room temperature for 48 h. The molecular sieves were removed by filtration and the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by column chromatography on silica gel using chloroform/ethyl acetate (100:3) to get the product as an oil (67 g, 47%). This product was a mixture of cis and trans isomers.

Workup

  1. customThe molecular sieves were removed by filtration
  2. customthe solvent was evaporated from the filtrate under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2f019379e9124518a3a1e9683211be2e
Source dataset
uspto-grants-2001_01
Patent number
US06172066B2

Reaction notes

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