Triphenylphosphine → (Cyclopentylmethyl)triphenylphosphonium iodide

HRID 1355166Notes

Reaction equation

HRID 1355166 reaction equation
[I:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C>[I-:1].[CH:3]1([CH2:2][P+:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 2762531(Iodomethyl)cyclopentane

Product 1

HCID 22315319(Cyclopentylmethyl)triphenylphosphonium iodideYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of iodomethylcyclopentane (129.38 g, 0.616 mol) and triphenylphosphine (161.54 g, 0.616 mol) in acetonitrile (308 mL) was heated under reflux for 9 d. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to provide a solid. The solid was triturated with diethyl ether and then filtered. The solid was washed well with diethyl ether until the washings showed the absence of iodomethylcyclopentane and triphenylphosphine by thin layer chromatography. The resulting solid was allowed to air dry to afford cyclopentylmethyl triphenylphosphonium iodide (266.92 g, 92%) as a light yellow solid: mp 195–198° C.; FAB-HRMS m/e calcd for C24H26P (M+H)+ 345.1772, found 345.1784.

Workup

  1. temperatureunder reflux for 9 d
  2. concentrationconcentrated in vacuo
  3. customto provide a solid
  4. customThe solid was triturated with diethyl ether
  5. filtrationfiltered
  6. washThe solid was washed well with diethyl ether until the washings
  7. customto air dry

Sources & evidence

ORD record
ord-b3869714a2474207bee05c0c9ce41bce
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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