Triphenylphosphine → {3-[(Oxan-2-yl)oxy]propyl}(triphenyl)phosphanium iodide

HRID 652462

Reaction equation

HRID 652462 reaction equation
[I: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>C1C=CC=CC=1>[I-: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

4

Reactant 2

HCID 11776TriphenylphosphineHCID 110329072-(3-iodopropoxy)tetrahydro-2H-pyran

Product 1

HCID 20196785{3-[(Oxan-2-yl)oxy]propyl}(triphenyl)phosphanium iodide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-iodo-1-tetrahydro-2-pyranyloxy propane (20.43 g, 75.63 mmole), and triphenylphosphine (19.84 g, 75.63 mmole) in 150 ml of dry benzene was refluxed under an atmosphere of nitrogen for 24 hours. The solvent was evaporated in vacuo to give a sticky gum. This was rinsed with acetonitrile (80 ml) when a white solid precipitated out. The solid was filtered and dried over phosphorous pentoxide at 60° C. in vacuo for 20 hours to give 32.8 g of the title B compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give a sticky gum
  3. washThis was rinsed with acetonitrile (80 ml) when a white solid
  4. customprecipitated out
  5. filtrationThe solid was filtered
  6. dry with materialdried over phosphorous pentoxide at 60° C. in vacuo for 20 hours
  7. customto give 32.8 g of the title B compound

Sources & evidence

ORD record
ord-6a76c51b19744678acb75cc8d37e39e0
Source dataset
uspto-grants-1987_06
Patent number
US04672075

Linked notes

Loading…