Triphenylphosphine → HCID 59571732, compound

HRID 2194307Notes

Reaction equation

HRID 2194307 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][N:20]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([O:33]CC=C)[C:27]=3[C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:17][C:16]=1[O:39][CH3:40].O1CCCC1CCO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][N:20]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([OH:33])[C:27]=3[C:26]3[C:21]2=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:17][C:16]=1[O:39][CH3:40]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 119895722-(Oxolan-2-yl)ethan-1-olHCID 59571733HCID 59571733, compound

Product 1

HCID 59571732HCID 59571732, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 284Formic AcidSolvent

Procedure

10 g of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-4-(allyloxy)-9H-carbazole was suspended in mixed solution (70 mL) of tetrahydrofuran-ethanol=4:1, 986 mg of triphenylphosphine, 84 mg of palladium acetate, and 2.1 mL of formic acid were added, and refluxed for 5 hours. The reaction mixture was allowed to cool, and then concentrated in vacuo, and the residue was crystallized from 10 mL of ethanol. The crystalline precipitate was isolated by filtration, washed with ethanol, dried under reduced pressure, and 8.96 g of the subject compound was prepared as pale yellow crystal.

Workup

  1. additionwere added
  2. temperaturerefluxed for 5 hours
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. customthe residue was crystallized from 10 mL of ethanol
  6. customThe crystalline precipitate was isolated by filtration
  7. washwashed with ethanol
  8. dry with materialdried under reduced pressure, and 8.96 g of the subject compound
  9. customwas prepared as pale yellow crystal

Sources & evidence

ORD record
ord-53c25cbe7ceb46ad977763f2db5cdcb5
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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