Chlorotrimethylsilane → 2-[Di(1-naphthyl)phosphino]phenylphosphine

HRID 1168638Notes

Reaction equation

HRID 1168638 reaction equation
C[Si](Cl)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:12]1([P:22]([C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38][CH:37]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[P:29](OCC)OCC)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O.C1COCC1>[C:12]1([P:22]([C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38][CH:37]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[PH2:29])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 11488538Diethyl 2-[di(1-naphthyl)phosphino]phenylphosphoniteHCID 21226445Aluminium lithium hydride

Product 1

HCID 111768752-[Di(1-naphthyl)phosphino]phenylphosphineYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen atmosphere, 5.74 g (52.9 mmol) of trimethylsilyl chloride was added dropwise to a 75 mL THF suspension of 2.01 g (52.9 mmol) of lithium aluminum hydride at −30° C. over a period of 30 minutes, and after the dropwise addition, the whole was stirred at room temperature for 1.5 hours. Then, a 50 mL THF solution of 8.50 g (17.6 mmol) of diethyl 2-[di(1-naphthyl)phosphino]phenylphosphonite (7) was added dropwise at −30° C. over a period of 30 minutes and the whole was stirred at room temperature for 16 hours. Thereto was gradually added dropwise a 15 mL THF solution of 7.5 mL of water at 0° C. to 10° C., and then 30 mL of 1N sodium hydroxide aqueous solution was added. Under a nitrogen atmosphere, the organic layer was decanted and the solvent was removed by evaporation. The residue was dissolved in 30 mL of diethyl ether, and the solution was washed three times with 10 mL of water degassed beforehand and then, dried over anhydrous sodium sulfate. The drying agent was removed and the solvent was removed by evaporation to obtain the title compound (6.50 g, a white viscous solid). Yield 93.5%.

Workup

  1. additionafter the dropwise addition
  2. stirringthe whole was stirred at room temperature for 16 hours
  3. customUnder a nitrogen atmosphere, the organic layer was decanted
  4. customthe solvent was removed by evaporation
  5. dissolutionThe residue was dissolved in 30 mL of diethyl ether
  6. washthe solution was washed three times with 10 mL of water degassed beforehand
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was removed
  9. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-46ffc8ad69c6409f8f83ce15e0dd6357
Source dataset
uspto-grants-2003_09
Patent number
US06624320B2

Reaction notes

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