3,4-Difluorobenzaldehyde → HCID 54260394, compound

HRID 1976590Notes

Reaction equation

HRID 1976590 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:16])[CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[F:26])[CH:21]=O>C1C=CC=CC=1.C([O-])(=O)C.[NH2+]1CCCCC1>[F:17][C:18]1[CH:19]=[C:20]([CH:21]=[C:5]([C:4](=[O:16])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH:23]=[CH:24][C:25]=1[F:26]

Participants

5

Reactant 2

HCID 5880883,4-DifluorobenzaldehydeHCID 22570139HCID 22570139, compound

Product 1

HCID 54260394HCID 54260394, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 3014295Piperidinium acetateCatalystHCID 241BenzeneSolvent

Procedure

To a solution of benzyl 4-methoxyacetoacetate (84 g, 0.37 mol), 3,4-difluorobenzaldehyde (52.5 g, 0.0.37 mmol), and piperidinium acetate (1.58 g, 2.63 mmol) in benzene (1L) 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 a white powder (118 g, 91%). The NMR showed this product to be 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-6ffda977e14142d7a164f15a5a789f74
Source dataset
uspto-grants-2001_05
Patent number
US06228861B1

Reaction notes

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