Di[p-(3-phenylpropyl)phenyl]chlorophosphine → Di[p-(3-phenylpropyl)phenyl]phosphine

HRID 1638232Notes

Reaction equation

HRID 1638232 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([P:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:20][CH:19]=3)Cl)=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:27]1([CH2:26][CH2:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([PH:16][C:13]3[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:15][CH:14]=3)=[CH:19][CH:20]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 11113246Di[p-(3-phenylpropyl)phenyl]chlorophosphine

Product 1

HCID 19347535Di[p-(3-phenylpropyl)phenyl]phosphine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di[p-(3-phenylpropyl)phenyl]chlorophosphine 1 (6.0 g, 13.1 mmol) was dissolved in 150 ml THF and Li (0.185 g, 26.2 mmol) was chopped directly into the reaction flask under Ar. A deep red solution was resulted in 10 min and all the lithium was consumed in 4 h. The solvent was removed by vacuum and 100 ml diethyl ether was added. The organic phase was washed 3×20 ml H2O and dried over MgSO4. Ether was then removed by vacuum and the final product was obtained as a pale yellow oil with quantitative yield. 2 was characterized by 31P NMR. -42.5, 1JH-P =211 Hz.

Workup

  1. customA deep red solution was resulted in 10 min
  2. customall the lithium was consumed in 4 h
  3. customThe solvent was removed by vacuum and 100 ml diethyl ether
  4. additionwas added
  5. washThe organic phase was washed 3×20 ml H2O
  6. dry with materialdried over MgSO4
  7. customEther was then removed by vacuum

Sources & evidence

ORD record
ord-bbad41c8f0244675a7981b4fe93ff873
Source dataset
uspto-grants-2000_03
Patent number
US06043398

Reaction notes

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