Methyl 4-methoxyacetoacetate → HCID 54115946, compound

HRID 1976582Notes

Reaction equation

HRID 1976582 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-55b80c67558e4b89bc00a446b8387bba
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

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