Cesium carbonate → HCID 57532176, compound

HRID 1455263Notes

Reaction equation

HRID 1455263 reaction equation
Cl[CH:2]([C:6](=[O:8])[CH3:7])[C:3](=[O:5])[CH3:4].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)#[N:10].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[C:3]([CH:2]([O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][CH:13]=1)[C:6](=[O:8])[CH3:7])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 130194-CyanophenolHCID 743283-Chloro-2,4-pentanedione

Product 1

HCID 57532176HCID 57532176, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of commercially available 3-chloro-2,4-pentanedione (14.01 ml, 92 mmol), 4-cyanophenol (10 g, 84 mmol), caesium carbonate (29.9 g, 92 mmol) and acetone (160 ml) was heated under reflux for 5 hours. After cooling, a solid was removed by filtration and it was washed with dichloromethane (100 ml). The combined filtrates were concentrated under reduced pressure. The remaining oil was diluted with dichloromethane (150 ml), washed with 1M hydrochloric acid (100 ml), then brine (50 ml), dried over magnesium sulphate, filtered and finally concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (15:1, by volume then 10:1) to provide the title compound, which crystallised on standing, as pale yellow crystals (7.27 g, 39.6%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. customa solid was removed by filtration and it
  5. washwas washed with dichloromethane (100 ml)
  6. concentrationThe combined filtrates were concentrated under reduced pressure
  7. additionThe remaining oil was diluted with dichloromethane (150 ml)
  8. washwashed with 1M hydrochloric acid (100 ml)
  9. dry with materialbrine (50 ml), dried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationfinally concentrated under reduced pressure
  12. customThe crude product was purified by flash chromatography on silica gel eluting with pentane:ethyl acetate (15:1

Sources & evidence

ORD record
ord-84345426c6fa43ffa91e1e2e1f69cbb4
Source dataset
uspto-grants-2009_01
Patent number
US07482375B2

Reaction notes

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