Lithium iodide → 2,3,5,6-Tetrahydro-3-(2-methoxy)ethylthiopyran-4-one

HRID 1381687Notes

Reaction equation

HRID 1381687 reaction equation
C([C:5]1([CH2:12][CH2:13][O:14][CH3:15])[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1)(OC)=O.[I-].[Li+].O.Cl>CN(C=O)C>[CH3:15][O:14][CH2:13][CH2:12][CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1

Participants

5

Reactant 3

HCID 66321Lithium iodideHCID 21276494HCID 21276494, compoundHCID 21885828Hydrate;hydrochloride

Product 1

HCID 212765012,3,5,6-Tetrahydro-3-(2-methoxy)ethylthiopyran-4-oneYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.4 g (10.3 mmol) of product from Step A in 50 ml DMF was added 6 g (44.8 mmol) lithium iodide. The resulting solution was refluxed under N2 for 2 hours. The reaction mixture was poured into 500 ml H2O/HCl and extracted with ethyl acetate. THe organic solution was washed with water; saturated NaCl, dried over MgSO4 and concentrated in vacuo to give 1.7 g crude product which was chromatographed through a pressure column eluting with 10% ethyl acetate/n-hexane to give 0.9 g of title compound.

Workup

  1. temperatureThe resulting solution was refluxed under N2 for 2 hours
  2. extractionextracted with ethyl acetate
  3. washTHe organic solution was washed with water
  4. dry with materialsaturated NaCl, dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give 1.7 g crude product which
  7. customwas chromatographed through a pressure column
  8. washeluting with 10% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-bde03a1913b746bfa68127fc4b3b23db
Source dataset
uspto-grants-1989_02
Patent number
US04803286

Reaction notes

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