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

HRID 1269412Notes

Reaction equation

HRID 1269412 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

Procedure

Subsequently, to a suspension of (1-methylpyrrol-2-yl)methyl trimethylammonium iodide (55.34 g, 197.5 mmol) obtained above in acetonitrile (400 ml) was added triphenylphosphine (62.20 g, 237.1 mmol) with stirring, and the resulting mixture was stirred at 80° C. for 10 hours. After cooling, the reaction mixture was concentrated to about one-half of its initial volume, to which was added ethyl acetate (200 ml). The crystals precipitated were collected by filtration, washed with ethyl acetate and dried in vacuo to afford the title compound (77.14 g, yield: 81%).

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for 10 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated to about one-half of its initial volume
  4. additionto which was added ethyl acetate (200 ml)
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. washwashed with ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3c15498b3a3e458981610e92febdef5f
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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