Methyl acetoacetate → methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate

HRID 1452653Notes

Reaction equation

HRID 1452653 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[O:10]=[C:11]([CH3:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14].N1CCCCC1>C1C=CC=CC=1>[C:11](/[C:12](=[CH:6]/[C:5]1[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=1)/[C:13]([O:15][CH3:16])=[O:14])(=[O:10])[CH3:17]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 10751489methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoateYield 99.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-fluorobenzaldehyde (25.5 g, 0.220 mol), methyl 3-oxobutanoate (21.80 g, 0.220 mol), and piperidine (1.0 mL) in anhydrous benzene (250 mL) was stirred for 10 minutes at room temperature and subsequently refluxed overnight in a Dean-Stark apparatus. The reaction mixture was then cooled to room temperature and the solvent was removed in vacuo to afford methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate as a black solid (48.6 g, 99%), which was used for next step without purification.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f8d2dc2f96b3472689064f9609a1b8b9
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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