2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde → Ethyl 3-oxopent-4-enoate

HRID 1272580Notes

Reaction equation

HRID 1272580 reaction equation
[O:1]=[C:2](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][C:4]([O-])=O.C1(C2C(C=O)=C(C3C=CC(F)=CC=3)C3C(=CC=CC=3)N=2)CC1.CCCCCC.[CH2:55]([O:57][C:58](=[O:60])[CH3:59])[CH3:56]>C(#N)C>[CH2:55]([O:57][C:58](=[O:60])[CH2:59][C:2](=[O:1])[CH:3]=[CH2:4])[CH3:56]

Participants

5

Reactant 3

HCID 99479742-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehydeHCID 184577483-Oxo-4-(triphenylphosphoranylidene)butanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 12536080Ethyl 3-oxopent-4-enoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The ylide 3-oxo-4-(triphenylphosphoranylidene)butanoate (4.82 g, 12.36 mmol) is solved under argon atmosphere in 100 ml acetonitrile. Under vigorous stirring 2-cyclopropyl-4-(4-fluoro-phenyl)-quinoline-3-carbaldehyde (3 g, 10.3 mmol) is added in 5 portions and then heated to reflux. After 50 h the reaction is cooled to room temperature. The slight brown solvent is evaporated and the residue is dried under vacuum to obtain a brown waxy oil. Chromatography over silica gel with hexane:ethylacetate (4:1/v:v) give a yellow oil of 5-(2-cyclopropyl-4-fluoro-phenyl)-quinolin-3-yl)-3-oxo-pent-4-enoic acid ethyl ester. MS: 403.45

Workup

  1. additionis added in 5 portions
  2. temperatureheated to reflux
  3. customThe slight brown solvent is evaporated
  4. customthe residue is dried under vacuum
  5. customto obtain a brown waxy oil

Sources & evidence

ORD record
ord-eac26cf701ce4b62a360dc098f6af053
Source dataset
uspto-grants-2007_04
Patent number
US07208623B2

Reaction notes

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