Pyridine → HCID 11355780, compound

HRID 557425Notes

Reaction equation

HRID 557425 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:30])[CH:10]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:31](OC(=O)C)(=O)[CH3:32].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:31][C:32]1[O:1][C:2]2[C:3]([C:9](=[O:30])[CH:10]=1)=[CH:4][CH:5]=[CH:6][C:7]=2[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14985947HCID 14985947, compound

Product 1

HCID 11355780HCID 11355780, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

27.5 g (67 mmol) of 1-(2-hydroxy-3-methylphenyl)-2-(triphenylphosphoranylidene)ethanone are heated to reflux in 200 ml of absolute toluene. 13.7 g (134 mmol) of acetic anhydride and 11.1 g (141 mmol) of pyridine are slowly added dropwise to this solution. The reaction mixture is then heated under reflux for 6 h. After cooling to room temperature, the solution is washed with saturated sodium carbonate solution and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate 7:3→4:6). 7.5 g (64% of theory) of the title compound are obtained.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 6 h
  3. washthe solution is washed with saturated sodium carbonate solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by column chromatography (mobile phase: cyclohexane/ethyl acetate 7:3→4:6)

Sources & evidence

ORD record
ord-7d662f9b98aa4b1886052fa2b8a7f626
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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