p-Toluenesulfonic acid → HCID 68109162, compound

HRID 2179371Notes

Reaction equation

HRID 2179371 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 290124-Iodobenzyl alcohol

Product 1

HCID 68109162HCID 68109162, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-iodobenzyl alcohol (2.0 g, 8.54 mmol) in dry dichloromethane (15 mL) was added 3,4-dihydro-2H-pyran (0.92 mL, 10.25 mmol) followed by p-toluenesulfonic acid (147 mg, 0.85 mmol). The reaction mixture was stirred at ambient temperature for 2 h under a nitrogen atmosphere before partitioning between water and dichloromethane. The organic layer was washed with water followed by brine solution then dried over Na2SO4. After concentration in vacuo the residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give 2-(4-iodobenzyloxy)tetrahydro-2H-pyran (2.0 g, 74%) as a colorless liquid: 1H NMR (CDCl3, 400 MHz) δ 8.12 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 4.76-4.65 (m, 2H), 4.46 (d, J=12.0 Hz, 1H), 3.94-3.84 (m, 1H), 3.59-3.49 (m, 1H), 1.91-1.49 (m, 6H).

Workup

  1. custombefore partitioning between water and dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialthen dried over Na2SO4
  4. concentrationAfter concentration in vacuo the residue
  5. customwas purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ebe4e6c2be2f4d829e36ea92478acc7e
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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