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

HRID 2309427Notes

Reaction equation

HRID 2309427 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 a saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was flash chromatographed on a silica gel to give 20.43 g of title A compound as an oil, with consistent spectral data.

Workup

  1. washwashed with water
  2. dry with materiala saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customchromatographed on a silica gel

Sources & evidence

ORD record
ord-c9f9add0997945bfba43c49be4866b9c
Source dataset
uspto-grants-1987_09
Patent number
US04695585

Reaction notes

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