Triphenylphosphine → (Cyclopentylmethyl)triphenylphosphonium iodide

HRID 1860183Notes

Reaction equation

HRID 1860183 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 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of iodomethylcyclopentane (4.60 g, 21.89 mmol) and triphenylphosphine (5.74 g, 21.89 mmol) in acetonitrile (22 mL) was heated under reflux for 2 weeks. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to provide an orange solid. The orange 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 solid was allowed to air dry to afford cyclopentylmethyl triphenylphosphonium iodide (8.92 g, 86%) as a light orange solid: mp 195-198° C.; FAB-HRMS m/e calcd for C24H26P (M+H)+345.1772, found 345.1784.

Workup

  1. temperatureunder reflux for 2 weeks
  2. concentrationconcentrated in vacuo
  3. customto provide an orange solid
  4. customThe orange 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-b84b120a236246bd9f8a0d9fc8f1bd5e
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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