Diethyl Ether → Phosphine, 1H-inden-1-yldiphenyl-

HRID 1387658Notes

Reaction equation

HRID 1387658 reaction equation
[CH-:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].CCOCC.[C:16]1([P:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)Cl)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH:1]1([P:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 66180ChlorodiphenylphosphineHCID 11116044Lithium, 1H-inden-1-yl-

Product 1

HCID 12074547Phosphine, 1H-inden-1-yldiphenyl-Yield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the drybox lithium indenide (8.00 g, 65.52 mmol) dissolved in 50 mL of THF was added within 15 minutes to a 180 mL ether solution of diphenylchlorophosphine (14.46 g, 65.52 mmol) (diphenylchlorophosphine was distilled before use (97° C. @ 0.4 torr)). After stirring overnight, LiCl was separated by filtration giving a yellow solution. Solvent was removed under vacuum leaving an off-white solid. This solid was triturated with 40 mL of hexane. Hexane was removed by decanting and the solid was dried under reduced pressure to give 16.43 g of off-white solid. Yield 84 percent.

Workup

  1. customLiCl was separated by filtration
  2. customgiving a yellow solution
  3. customSolvent was removed under vacuum
  4. customleaving an off-white solid
  5. customThis solid was triturated with 40 mL of hexane
  6. customHexane was removed
  7. customby decanting
  8. customthe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-e5eba6eaea484f278dfc49b2ef32fa2d
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

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