Phosphine → HCID 22237099, compound

HRID 1635715Notes

Reaction equation

HRID 1635715 reaction equation
F[B-](F)(F)F.[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[O+]=1.[PH3:32]>C(O)CCC>[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[C:15]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[P:32]=1

Participants

4

Reactant 2

HCID 24404PhosphineHCID 18676579HCID 18676579, compound

Product 1

HCID 22237099HCID 22237099, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The reaction was carried out twice using 15 g (35 mmol) each time of 2,6-bis(2-methylphenyl)-4-phenylpyrylium tetrafluoroborate in 150 ml of n-butanol. The two autoclave products obtained after the reaction with PH3 were combined and evaporated to about 50 ml under reduced pressure at about 80° C. The solid which precipitated was filtered off with suction, washed with n-pentane and subsequently dissolved in toluene. The toluene solution was then washed with water until the aqueous phase was neutral. After removal of the solvent, the residue was suspended in methanol, and dichloromethane was then added until the solid had completely dissolved. The resulting solution was evaporated under reduced pressure at about 40° C. until a solid precipitated. The solid was filtered off with suction, washed with a little n-pentane and subsequently dried in a high vacuum. Yield: 15.6 g (63%) of white solid.

Workup

  1. customThe two autoclave products obtained
  2. customevaporated to about 50 ml under reduced pressure at about 80° C
  3. customThe solid which precipitated
  4. filtrationwas filtered off with suction
  5. washwashed with n-pentane
  6. dissolutionsubsequently dissolved in toluene
  7. washThe toluene solution was then washed with water until the aqueous phase
  8. customAfter removal of the solvent
  9. additiondichloromethane was then added until the solid
  10. dissolutionhad completely dissolved
  11. customThe resulting solution was evaporated under reduced pressure at about 40° C. until a solid
  12. customprecipitated
  13. filtrationThe solid was filtered off with suction
  14. washwashed with a little n-pentane
  15. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-6beb0b9b240b4a53a8af8271aa50eda7
Source dataset
uspto-grants-2003_01
Patent number
US06509505B1

Reaction notes

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