Propylene Glycol → HCID 14880907, compound

HRID 2165501Notes

Reaction equation

HRID 2165501 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](O)[CH:17]([OH:19])[CH3:18].B(F)(F)F.CCOCC.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:15][C:12]1[N:11]=[CH:10][C:9]([C:1]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:19][CH:17]([CH3:18])[CH2:16][O:8]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 3061713Methanone, (6-chloro-3-pyridinyl)phenyl-

Product 1

HCID 14880907HCID 14880907, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 25 ml of a solution of 1.5 g of 3-benzoyl-6-chloropyridine and 3.2 g of 1,2-propanediol in toluene, 1.2 g of boron trifluoride etherate was added. The resulting mixture was heated under reflux for six hours while removing the water thus formed therefrom. Then the reaction mixture was cooled, poured into an aqueous solution of sodium hydroxide and extracted with ether. The organic phase was washed with water and dried over anhydrous sodium sulfate. After filtering off the sodium sulfate and distilling off the solvent in vacuo, 2-(6-chloropyridin-3-yl)-4-methyl-2-phenyl-1,3-dioxolane was obtained, m.p.: 44°-51° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for six hours
  3. customwhile removing the water
  4. customthus formed
  5. temperatureThen the reaction mixture was cooled
  6. extractionextracted with ether
  7. washThe organic phase was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtering off the sodium sulfate
  10. distillationdistilling off the solvent in vacuo

Sources & evidence

ORD record
ord-568c01c7b9284472a8ad5bfce5f8366d
Source dataset
uspto-grants-1990_07
Patent number
US04940483

Reaction notes

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