Triphenylphosphine → (1-Ethylpyrrol-2-yl)methyltriphenylphosphonium iodide

HRID 604558Notes

Reaction equation

HRID 604558 reaction equation
[I-:1].[CH2:2]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][N+](C)(C)C)[CH3:3].[C:14]1([P:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[I-:1].[CH2:2]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][P+:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:3]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23031652(1-Ethylpyrrol-2-yl)methyltrimethylammonium iodide

Product 1

HCID 23031502(1-Ethylpyrrol-2-yl)methyltriphenylphosphonium iodideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(1-Ethylpyrrol-2-yl)methyltrimethylammonium iodide (20.0 g, 68.0 mmol) was suspended in acetonitrile (200 mL) and triphenylphosphine (22.0 g, 83.9 mmol) was added thereto, followed by stirring of the mixture at 80° C. for 9 hours. After cooling, the mixture was concentrated to about ½ under reduced pressure and ethyl acetate (100 mL) was added thereto. The precipitated crystal was collected by filtration, washed with ethyl acetate and dried under reduced pressure to obtain the title compound (27.5 g, yield: 81%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to about ½ under reduced pressure and ethyl acetate (100 mL)
  3. additionwas added
  4. filtrationThe precipitated crystal was collected by filtration
  5. washwashed with ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-e283bf67d68a492ea769b0c54cf146cf
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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