Triphenylphosphine → [(3,5-Dimethyl-1,2-oxazol-4-yl)methyl](triphenyl)phosphanium chloride

HRID 1287686Notes

Reaction equation

HRID 1287686 reaction equation
[Cl:1][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[Cl-:1].[CH3:9][C:4]1[C:3]([CH2:2][P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:7]([CH3:8])[O:6][N:5]=1

Participants

3

Reactant 2

HCID 11776TriphenylphosphineHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-

Product 1

HCID 20362358[(3,5-Dimethyl-1,2-oxazol-4-yl)methyl](triphenyl)phosphanium chloride

Procedure

A solution of 59.6 g. (0.402 mole) of 4-chloromethyl-3,5-dimethylisoxazole, prepared as described above, and 116 g. (0.44 mole) of triphenylphosphine in 1 liter of tolune was heated at reflux under nitrogen for 6 hours. The resulting suspension was cooled and filtered. The filtrate was heated at reflux for an additional 20 hours. The precipitate was again removed by filtration and the combined solids were washed well with ether and benzene. The solvent was removed from the filtrate and the residue was taken up in 150 ml. of fresh toluene and refluxed for an additional 18 hours. Filtration as before gave another small quantity of solid. The combined solids were crystallized from ethanol-ether to give the desired phsophonium salt as a cream-white solid, m.p. 313°-316°.

Workup

  1. temperatureat reflux under nitrogen for 6 hours
  2. temperatureThe resulting suspension was cooled
  3. filtrationfiltered
  4. temperatureThe filtrate was heated
  5. temperatureat reflux for an additional 20 hours
  6. customThe precipitate was again removed by filtration
  7. washthe combined solids were washed well with ether and benzene
  8. customThe solvent was removed from the filtrate
  9. temperatureof fresh toluene and refluxed for an additional 18 hours
  10. filtrationFiltration as
  11. custombefore gave another small quantity of solid
  12. customThe combined solids were crystallized from ethanol-ether
  13. customto give the desired phsophonium salt as a cream-white solid, m.p. 313°-316°

Sources & evidence

ORD record
ord-6572459f6b16495992f0e92578ca6647
Source dataset
uspto-grants-1976_10
Patent number
US03985771

Reaction notes

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