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

HRID 1029404Notes

Reaction equation

HRID 1029404 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 ##STR11## (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
  3. customThe residue was 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-e68f4b6c308d4719a31241ae3bb01729
Source dataset
uspto-grants-1992_04
Patent number
US05102878

Reaction notes

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