Triphenylphosphine → HCID 21273347, compound

HRID 1382918Notes

Reaction equation

HRID 1382918 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][CH2:8][CH2:7][C:6]2([CH3:14])[CH3:13].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][P+:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:4]=2)[O:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13983022HCID 13983022, compound

Product 1

HCID 21273347HCID 21273347, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.25 g (28.4 mmole) of 6-bromomethyl-4,4-dimethylchroman, 14.8 g (56.8 mmole) of triphenylphosphine and 100 ml of toluene were heated under reflux for 12 hours, and then the solvent was removed by evaporation in vacuo. The residue (an oil) was dissolved in dichloromethane and decolorized with activated carbon. The solvent was removed by evaporation in vacuo and the residue was triturated under hexane to remove starting materials. The product so obtained was recrystallized from toluene-chloroform and the solid was discarded. The recrystallization mother liquors were evaporated in vacuo and the oily residue was triturated under 1N hydrochloric acid and then dissolved in dichloromethane. This latter solution was dried (MgSO4) and evaporated in vacuo to give 5.2 g of the title compound as a light brown solid.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 12 hours
  3. customthe solvent was removed by evaporation in vacuo
  4. dissolutionThe residue (an oil) was dissolved in dichloromethane
  5. customThe solvent was removed by evaporation in vacuo
  6. customthe residue was triturated under hexane
  7. customto remove
  8. customThe product so obtained
  9. customwas recrystallized from toluene-chloroform
  10. customThe recrystallization mother liquors were evaporated in vacuo
  11. customthe oily residue was triturated under 1N hydrochloric acid
  12. dissolutiondissolved in dichloromethane
  13. dry with materialThis latter solution was dried (MgSO4)
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-283b7b7813694d2daa51ed6208304d04
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

Loading…