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

HRID 1791118Notes

Reaction equation

HRID 1791118 reaction equation
C(O)(=O)C.N1CCCCC1.[Cl:11][C:12]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[CH:14]=O.[C:21]([O:27][CH3:28])(=[O:26])[CH2:22][C:23]([CH3:25])=[O:24]>C(O)(C)C>[C:23]([C:22](=[CH:14][C:13]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:12]=1[Cl:11])[C:21]([O:27][CH3:28])=[O:26])(=[O:24])[CH3:25]

Participants

5

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 1

HCID 3776IsopropanolSolvent

Procedure

1.7 ml of piperidine acetate are added to a solution of 50 g (315 mmol) of 2-chloro-4-fluorobenzaldehyde and 36.6 g (315 mmol) of methyl acetoacetate in 150 ml of isopropanol. Stirring at room temperature overnight is followed by dilution with dichloromethane and extraction with water, and the organic phase is dried over sodium sulfate and concentrated. The product is reacted further as a crude cis/trans mixture.

Workup

  1. extractionis followed by dilution with dichloromethane and extraction with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product is reacted further as a crude cis/trans mixture

Sources & evidence

ORD record
ord-fa415c37887b4ae1b30cfd84fac67006
Source dataset
uspto-grants-2006_07
Patent number
US07074784B2

Reaction notes

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