3,4-dihydro-2H-pyran → 2-(3-Iodophenoxy)oxane

HRID 2245891Notes

Reaction equation

HRID 2245891 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>C(Cl)Cl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyran2×HCID 122723-Iodophenol2×

Product 1

HCID 588159442-(3-Iodophenoxy)oxaneYield 92.1%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)Catalyst2×HCID 6344DichloromethaneSolvent

Procedure

The solution of 3-iodophenol (70.31 g), PPTS (750 mg) and 3,4-dihydro-2H-pyran (55.68 g) in CH2Cl2 (400 mL) was refluxed under N2 for 3 h. TLC of the reaction solution indicated the presence of starting material, 3-iodophenol. Consequently, more 3,4-dihydro-2H-pyran (30 mL) and PPTS (350 mg) were added to the reaction solution. The reaction was refluxed for another 3 h. After being cooled to room temperature, the reaction solution was washed by saturated NaHCO3 (100 mL×2), H2O (120 mL×3) and brine (120 mL×1), dried by Na2SO4 and concentrated to give crude product, which was purified to give pure 2-(3-Iodo-phenoxy)-tetrahydro-pyran (89.5 g; 92%). 1H NMR (300 MHz, CDCl3) □ 7.42 (m, 1H), 7.31 (m, 1H), 7.00 (m, 2H), 5.39 (dd, 1H, J=3.0, 3.0 Hz), 3.87 (m, 1H), 3.61 (m, 1H), 1.97 (m, 1H), 1.84 (m, 2H), 1.65 (m, 3H).

Workup

  1. temperatureThe reaction was refluxed for another 3 h
  2. washthe reaction solution was washed by saturated NaHCO3 (100 mL×2), H2O (120 mL×3) and brine (120 mL×1)
  3. dry with materialdried by Na2SO4
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas purified

Sources & evidence

ORD record
ord-8def11352bf345f48368ccdf06afc7c4
Source dataset
uspto-grants-2010_03
Patent number
US07683168B2

Reaction notes

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