3,4-dihydro-2H-pyran → 2-[3-(4-iodophenyl)propoxy]tetrahydro-2H-pyran

HRID 254413Notes

Reaction equation

HRID 254413 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[I:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=1>C(Cl)(Cl)Cl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[I:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][O:17][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 30426144-Iodobenzenepropanol

Product 1

HCID 668730592-[3-(4-iodophenyl)propoxy]tetrahydro-2H-pyranYield 100%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6212ChloroformSolvent2×

Procedure

3,4-Dihydro-2H-pyran (2.5 mL, 27.4 mmol) and pyridinium p-toluenesulfonate (450 mg, 1.79 mmol) were added to a chloroform (50 mL) solution of 3-(4-iodophenyl)propan-1-ol (4.73 g, 18.0 mmol), and stirred overnight at room temperature. The reaction liquid was diluted with chloroform, washed with saturated saline, dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (C-200, ethyl acetate:hexane=1:9 to 1:4) to obtain the entitled compound (6.22 g, 100%).

Workup

  1. customThe reaction liquid
  2. washwashed with saturated saline
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (C-200, ethyl acetate:hexane=1:9 to 1:4)

Sources & evidence

ORD record
ord-dd735bb1839b410e89628ec8a01a1b2c
Source dataset
uspto-grants-2011_01
Patent number
US07875633B2

Reaction notes

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