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

HRID 562639Notes

Reaction equation

HRID 562639 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

Subsequently, to a suspension of (1-ethylpyrrol-2-yl)methyl trimethylammonium iodide (20 g, 68.0 mmol) obtained above in acetonitrile (200 ml) was added triphenylphosphine (22.0 g, 83.9 mmol), and the resulting mixture was stirred at 80° C. for 9 hours. After cooling, the reaction mixture was concentrated to about one-half of its initial volume, to which was added ethyl acetate (1.00 ml). The crystals precipitated were collected by filtration, washed with ethyl acetate and dried in vacuo to afford the title compound (27.5 g, yield: 81%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to about one-half of its initial volume
  3. additionto which was added ethyl acetate (1.00 ml)
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-1caf8e1db92c480f9e1ac405c40251c8
Source dataset
uspto-grants-2011_11
Patent number
US08067396B2

Reaction notes

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