Triphenylphosphine → HCID 86647481, compound

HRID 2192892Notes

Reaction equation

HRID 2192892 reaction equation
[I:1][CH2:2][CH:3]1[CH2:7][CH2:6][O: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].[C:21]1([P+:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH:3]2[CH2:7][CH2:6][O:5][CH2:4]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 27630063-(Iodomethyl)oxolane

Product 1

HCID 86647481HCID 86647481, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(iodomethyl)tetrahydrofuran (10.1 g) in acetonitrile (101 mL) was added triphenylphosphine (13.1 g), followed by heating under reflux for 1 week. The solution was concentrated under reduced pressure, followed by addition of diethyl ether. The resulting solid was collected by filtration and washed with diethyl ether to obtain triphenyl(tetrahydrofuran-3-ylmethyl)phosphonium iodide (18.8 g) as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 week
  3. concentrationThe solution was concentrated under reduced pressure
  4. additionfollowed by addition of diethyl ether
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9dfaef3f198a417fae35a3c13c41b5b9
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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