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

HRID 1869679Notes

Reaction equation

HRID 1869679 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 (100 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 (100 ml)
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. washwashed with ethyl acetate
  7. customdried in vacuo

Sources & evidence

ORD record
ord-273bee76b54446fe88f544dd876ce428
Source dataset
uspto-grants-2009_12
Patent number
US07638551B2

Reaction notes

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