3,4-dihydro-2H-pyran → 2-(3-iodopropoxy)tetrahydro-2H-pyran

HRID 2309416Notes

Reaction equation

HRID 2309416 reaction equation
[I:1][CH2:2][CH2:3][CH2:4][OH:5].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[I:1][CH2:2][CH2:3][CH2:4][O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 693903-Iodo-1-propanolHCID 21909214Pyridium p-toluenesulfonate

Product 1

HCID 110329072-(3-iodopropoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-iodopropanol (15 g, 80.65 mole), dihydropyran (14.7 ml, 161.29 mole) and pyridium p-toluenesulfonate (500 g, 2.0 mole) in 100 ml of dry dichloromethane was stirred at room temperature under an atmosphere of nitrogen for 2.5 hours. The resulting mixture was diluted with dichloromethane (150 ml), washed with water and saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was flash-chromatographed on a silica gel column to give 20.43 g of the title A compound as an oil with a consistent NMR spectrum.

Workup

  1. washwashed with water and saturated sodium bicarbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was flash-chromatographed on a silica gel column

Sources & evidence

ORD record
ord-96d1af28732241f093f60e0d65e073f3
Source dataset
uspto-grants-1987_09
Patent number
US04695586

Reaction notes

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