Triphenylphosphine → HCID 10907034, compound

HRID 1656310Notes

Reaction equation

HRID 1656310 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][O:7]1.[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Br-:1].[O:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[O:5][CH2:4][CH2:3][CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 10907034HCID 10907034, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

66.5 g (0.298 mol) of 2-(3-bromopropyloxy)tetrahydropyran is refluxed together with 82 g (0.312 mol) of triphenylphosphine and 1 g of tetrabutylammonium iodide in 500 ml of acetonitrile for 24 hours. After evaporation of the solvent, the residue is triturated several times with boiling diethylether. 144 g (100%) of 3-(tetrahydropyranyloxy)propyl-triphenylphosphonium bromide is obtained as heavy oil. (C26H30BrNO2P; F.W. 485.4).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is triturated several times with boiling diethylether

Sources & evidence

ORD record
ord-47b92af7f3494f3e8e49cef4403ffe84
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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