Triethylamine → Diphenylphosphine

HRID 990296Notes

Reaction equation

HRID 990296 reaction equation
Cl[SiH](Cl)Cl.[C:5]1([PH:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[C:12]1([PH:11][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 254003Diphenylphosphine oxide

Product 1

HCID 70017DiphenylphosphineYield 79%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Trichlorosilane (0.1 ml, 1 mmol) was added, at room temperature, to a suspension of (1H, 1H, 2H, 2H-perfluorooctyl)diphenylphosphine oxide (55 mg, 0.1 mmol) and triethylamine (0.1 ml, 0.7 mmol) in toluene (5 ml). The mixture was then heated at 100 C. overnight and then allowed to cool. Aqueous sodium hydroxide (40 ml of a 1M solution) was added and the resulting mixture extracted with ether (4×25 ml). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo to give the crude product. The product was purified by flash column chromatography on silica gel, eluting with hexane to give a white crystalline solid (42 mg, 0.079 mmol, 79%), mp (CH2Cl2) 44-45° C. (Found: M+,532.0600. C20H14F13P requires M+, 532.0625).

Workup

  1. temperatureThe mixture was then heated at 100 C
  2. customovernight
  3. temperatureto cool
  4. extractionthe resulting mixture extracted with ether (4×25 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe product was purified by flash column chromatography on silica gel
  9. washeluting with hexane

Sources & evidence

ORD record
ord-a7d524edd1a84c4e9f58d3db63dfac71
Source dataset
uspto-grants-2002_10
Patent number
US06458985B1

Reaction notes

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