Phosphorus oxychloride → HCID 19926464, compound

HRID 1647167Notes

Reaction equation

HRID 1647167 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][CH:7]1[C:12](=O)[CH:11]=[CH:10][N:9]=[C:8]1[CH3:14].O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([CH3:14])[C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 67810172HCID 67810172, compound

Product 1

HCID 19926464HCID 19926464, compoundYield 34%

Procedure

A solution of 3-(3-methoxy-1-propoxy)-2-methyl-4-pyridone (0.32 g, 1.6 mmol) in 50 ml POCl3 was refluxed for 14 h. The POCl3 was evaporated off and the residue was partitioned between methylene chloride and water. The aqueous layer was separated, treated with K2CO3 until pH=10 and extracted with methylene chloride. The organic layer was dried over Na2SO4 and evaporated. The residue was purified by chromatography on silica gel with methanol/methylene chloride (3:97) as eluent. Evaporation off the solvent afforded 0.12 g (34%) product as a red oil.

Workup

  1. customThe POCl3 was evaporated off
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe aqueous layer was separated
  4. additiontreated with K2CO3 until pH=10
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel with methanol/methylene chloride (3:97) as eluent
  9. customEvaporation off the solvent

Sources & evidence

ORD record
ord-e82f43bb78ee4e2096761665050a62bc
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

Loading…