1-(Triphenylphosphoranylidene)acetone → 4-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)-3-buten-2-one

HRID 1650749Notes

Reaction equation

HRID 1650749 reaction equation
[C:1]1([C:7]2[C:15]([CH:16]=O)=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]([CH3:21])=[O:20]>C1C=CC=CC=1>[C:1]1([C:7]2[C:15]([CH:16]=[CH:18][C:19](=[O:20])[CH3:21])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 151581792-Phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde

Product 1

HCID 539006394-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-phenylpyrazolo[1,5-a]-pyridine-3-carbaldehyde (0.50 g) and acetonylidenetriphenylphosphorane ##STR12## (0 82 g) in benzene (6 ml) was refluxed for 4 hours and then the solvent was evaporated in vacuo The residue was chromatographed on silica gel (20 g) with chloroform as an eluent. The fractions containing the object compound, were combined and evaporated in vacuo. The residue was recrystallized from ethanol to give crystals of 4-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-3-buten-2-one (trans isomer) (0.21 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customthe solvent was evaporated in vacuo The residue
  3. customwas chromatographed on silica gel (20 g) with chloroform as an eluent
  4. additionThe fractions containing the object compound
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a4a834de57ab4e769e3b546fcb93c368
Source dataset
uspto-grants-1990_05
Patent number
US04925849

Reaction notes

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