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

HRID 442024Notes

Reaction equation

HRID 442024 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>C1(C)C=CC=CC=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

4

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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 toluene 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 phosphonium 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

Sources & evidence

ORD record
ord-ae1085fff78f4b54a0c87f52439737c7
Source dataset
uspto-grants-1977_08
Patent number
US04044004

Reaction notes

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