Pyridine → HCID 11355780, compound

HRID 1669774Notes

Reaction equation

HRID 1669774 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 in 200 ml of absolute toluene are heated to reflux. 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-806b849e45e74e159072ae54fec90dd3
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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