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

HRID 604546Notes

Reaction equation

HRID 604546 reaction equation
[I-:1].[CH3:2][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][N+](C)(C)C.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[I-:1].[CH3:2][N:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 12346658N,N,N-Trimethyl(1-methyl-1H-pyrrol-2-yl)methanaminium iodide

Product 1

HCID 23031470(1-Methylpyrrol-2-yl)methyltriphenylphosphonium iodideYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(1-Methylpyrrol-2-yl)methyltrimethylammonium iodide (55.3 g, 198 mmol) was suspended in acetonitrile (400 mL) and triphenylphosphine (62.2 g, 237 mmol) was added thereto, followed by stirring of the mixture at 80° C. for 10 hours. After cooling, the mixture was concentrated to about 1/2 under reduced pressure, ethyl acetate (200 mL) was added thereto, and the precipitated crystal was collected by filtration. The crystal was washed with ethyl acetate and dried under reduced pressure to obtain the title compound (77.1 g, yield: 81%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated to about 1/2 under reduced pressure, ethyl acetate (200 mL)
  3. additionwas added
  4. filtrationthe precipitated crystal was collected by filtration
  5. washThe crystal was washed with ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-306edc649297446a8c868c087c7aeb76
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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