Methyl acetoacetate → Methyl 2-[(2-chloro-4-fluorophenyl)methylene]-3-oxobutanoate

HRID 2121445Notes

Reaction equation

HRID 2121445 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].C(O)(=O)C.N1CCCCC1>C(O)(C)C.C(Cl)Cl>[C:13]([C:12](=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[Cl:1])[C:11]([O:17][CH3:18])=[O:16])(=[O:14])[CH3:15]

Participants

6

Reactant 3

HCID 7757Methyl acetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 9793820Piperidine, acetate

Product 1

HCID 57252060Methyl 2-[(2-chloro-4-fluorophenyl)methylene]-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

50 g (315 mmol) of 2-chloro-4-fluoro-benzaldehyde and 36.6 g (315 mmol) of methyl acetoacetate are dissolved in 150 ml of isopropanol and admixed with 1.7 ml of piperadine acetate. The mixture is stirred at room temperature overnight and then diluted with methylene chloride and extracted with water, dried over sodium sulphate and concentrated. The crude product is reacted further, as cis-trans mixture.

Workup

  1. extractionextracted with water
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. customThe crude product is reacted further, as cis-trans mixture

Sources & evidence

ORD record
ord-f675262d25f245ec942c621efab08b4c
Source dataset
uspto-grants-2004_02
Patent number
US06696451B1

Reaction notes

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