Lithium → 2,2'-Phosphanediyldipyridine

HRID 870390Notes

Reaction equation

HRID 870390 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-d36fe9731ba548309a451d7058f50c3a
Source dataset
uspto-grants-2015_03
Patent number
US08969560B2

Reaction notes

Loading…