Lithium → 2,2'-Phosphanediyldipyridine

HRID 1048825Notes

Reaction equation

HRID 1048825 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[P:7](C1C=CC=CN=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1.[Li]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[PH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 11065346Pyridine, 2,2',2''-phosphinidynetris-

Product 1

HCID 129784732,2'-Phosphanediyldipyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The tris(pyridin-2-yl)phosphine (22.4 g, 85 mmol) was suspended in THF (400 ml). To this were added lithium granules (5.0 g, 720 mmol). The mixture was then stirred at room temperature for four hours. This gave an intense red solution. The solution was then filtered into a clean Schlenk flask to remove any un-reacted lithium metal. The solvent was then removed under vacuum and water (100 ml, degassed with nitrogen gas for 20 minutes) added. Ether (400 ml) was then added and the biphasic solution stirred for 20 minutes. The upper (organic) phase was then cannula transferred into a clean Schlenk flask and then dried under vacuum. This gave dark orange/red oil. Yield=15.1 g, 94% 31P{1H}NMR (121 MHz, CDCl3) ä; −33.8 (s, PPy2).

Workup

  1. customThis gave an intense red solution
  2. filtrationThe solution was then filtered into a clean Schlenk flask
  3. customto remove any un-reacted lithium metal
  4. customThe solvent was then removed under vacuum and water (100 ml, degassed with nitrogen gas for 20 minutes)
  5. additionadded
  6. additionEther (400 ml) was then added
  7. stirringthe biphasic solution stirred for 20 minutes
  8. customcannula transferred into a clean Schlenk flask
  9. customdried under vacuum

Sources & evidence

ORD record
ord-378f7ae349a4443988c989b97b9603e2
Source dataset
uspto-grants-2016_07
Patent number
US09381503B2

Reaction notes

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