1,3,5-Trioxane → 6,7-dihydro-4H-thieno[3,2-c]pyran

HRID 270653Notes

Reaction equation

HRID 270653 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].O1COCO[CH2:10]1>[Cl-].[In+3].[Cl-].[Cl-].C(#N)CCC>[S:1]1[C:2]2[CH2:6][CH2:7][O:8][CH2:10][C:3]=2[CH:4]=[CH:5]1

Participants

5

Reactant 2

HCID 80811,3,5-TrioxaneHCID 794002-Thiopheneethanol

Product 1

HCID 114691186,7-dihydro-4H-thieno[3,2-c]pyranYield 121.2%

Reagents, catalysts & solvents 2

HCID 159675indium(III)chlorideCatalystHCID 8008ButyronitrileSolvent

Procedure

10.0 g of 2-thiopheneethanol, 3.5 g of 1,3,5-trioxane, and 862 mg of indium(III) chloride were added to 1,500 mL of butyronitrile, and the resulting mixture was refluxed for 6 hours. The reaction product solution was cooled to room temperature and concentrated by evaporation under reduced pressure. The residue was distilled under reduced pressure to obtain 6.6 g (yield of 60%) of the title compound, of which analysis data were the same as obtained in Example 14.

Workup

  1. temperaturethe resulting mixture was refluxed for 6 hours
  2. concentrationconcentrated by evaporation under reduced pressure
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-efa264e3dca74563bf547189cf36dec9
Source dataset
uspto-grants-2008_11
Patent number
US07449580B2

Reaction notes

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