2,6-Dimethyl-4-pyranone → 4H-Thiopyran-4-one, 2,6-dimethyl-

HRID 1720042Notes

Reaction equation

HRID 1720042 reaction equation
[CH3:1][C:2]1O[C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:19][C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1

Participants

4

Reactant 2

HCID 138622,6-Dimethyl-4-pyranoneHCID 87949Lawesson's reagent2×

Product 1

HCID 33645644H-Thiopyran-4-one, 2,6-dimethyl-Yield 181.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2,6-Dimethyl-4-pyranone (0.25 g, 2.0 mmol) in toluene (10 ml) was treated with Lawesson's reagent (0.22 g, 1.1 mmol) and heated at 100° C. for 3h. A further quantity of Lawesson's reagent (0.22 g, 1.1 mmol) was added and the mixture heated at 100° C. for 0.75h. The mixture was allowed to cool, then purified on silica gel 60 eluting with ethanol and dichloromethane (1:9) to give the title compound (0.28 g, 98%).

Workup

  1. temperaturethe mixture heated at 100° C. for 0.75h
  2. temperatureto cool
  3. custompurified on silica gel 60 eluting with ethanol and dichloromethane (1:9)

Sources & evidence

ORD record
ord-bdb9ff05559444e8a9646b9db4462752
Source dataset
uspto-grants-1996_04
Patent number
US05504076

Reaction notes

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