Imidazole → HCID 10337655, compound

HRID 2257076Notes

Reaction equation

HRID 2257076 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:42]I>C1(C)C=CC=CC=1>[I:42][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 807IodineHCID 11776TriphenylphosphineHCID 9991728HCID 9991728, compound

Product 1

HCID 10337655HCID 10337655, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of 8-(4-methoxyphenyl)octan-1-ol (12.3 g, 52 mmol) in dry toluene (200 mL) under an argon atmosphere was added triphenylphosphine (17.8 g, 67.6 mmol) and imidazole (10.6 g, 156 mmol). After the imidazole had dissolved, I2 (17.1 g, 67.6 mmol) was added. The reaction was then heated at 65° C. for 30 minutes. Upon cooling to room temperature the reaction was concentrated to 1/4 volume. The remaining solution was diluted with Et2O and washed with H2O and brine and dried. (MgSO4). The solvent was removed and the resulting residue was dissolved in CH2Cl2 and applied to a flash chromatography column (silica). Elution with 2% EtOAc in hexane provided the product as a colorless oil (slight contamination with triphenylphosphine): 1H NMR (250 MHz CDCl3)δ7.08 (d, J=8.6 Hz, 2H, aryl), 6.82 (d, J=8.6 Hz, 2H, aryl), 3.78 (s, 3H, OCH3), 3.17 (t, J=7.4 Hz, 2H, I-CH2), 2.54 (t, J=7.6 Hz, 2H, benzylic), 1.85 (m, 2H, CH2), 1.60 (m, 2H, CH2), 1.31 (m, 8H, aliphatic); MS (CI): 364.2 (M+NH4).

Workup

  1. temperatureUpon cooling to room temperature the reaction
  2. concentrationwas concentrated to 1/4 volume
  3. additionThe remaining solution was diluted with Et2O
  4. washwashed with H2O and brine
  5. customdried
  6. customThe solvent was removed
  7. dissolutionthe resulting residue was dissolved in CH2Cl2
  8. washElution with 2% EtOAc in hexane
  9. customprovided the product as a colorless oil (slight contamination with triphenylphosphine)

Sources & evidence

ORD record
ord-ce7d71332d6d4a5c8c3e344d1d7cc0c9
Source dataset
uspto-grants-1997_08
Patent number
US05656636

Reaction notes

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