Imidazole → (2-(3-Iodopropoxy)ethyl)benzene

HRID 1734680Notes

Reaction equation

HRID 1734680 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:38]I>C1(C)C=CC=CC=1.CCOCC.C(#N)C>[I:38][CH2:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 190822593-(2-Phenylethoxy)propan-1-ol

Product 1

HCID 19420724(2-(3-Iodopropoxy)ethyl)benzene

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 3-(2-phenylethoxy)-1-propanol (2 g; 11 mmol) dissolved in toluene (50 ml), acetonitrile (50 ml), imidazole (2.2 g; 33 mmol) and triphenylphosphine (2.8 g; 11 mmol) is added iodine (2.8 g; 11 mmol). The reaction mixture is heated for 1 hour at 50° C., then it is cooled, diluted with Et2O, washed with 1N HCl, NaS2O3 solution, NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% ether/90% petroleum ether to obtain 1-iodo-3-(2-phenylethoxy)propane which is used directly in Step D.

Workup

  1. temperatureit is cooled
  2. washwashed with 1N HCl, NaS2O3 solution, NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-a19a50c44ea9431dab6333beab6f5c61
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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