Formaldehyde → 6,7-dihydro-4H-thieno[3,2-c]pyran

HRID 270651

Reaction equation

HRID 270651 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[CH2:9]=O.[In+3]>C(#N)C>[S:1]1[C:2]2[CH2:6][CH2:7][O:8][CH2:9][C:3]=2[CH:4]=[CH:5]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 794002-ThiopheneethanolHCID 105148Indium cation

Product 1

HCID 114691186,7-dihydro-4H-thieno[3,2-c]pyranYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.0 g of 2-thiopheneethanol, 2.8 g of paraformaldehyde, and 2.2 g of indium(III) triplate were added to 780 mL of acetonitrile, and the resulting mixture was refluxed for 12 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 4.7 g (yield of 43%) of the title compound, of which analysis data were the same as obtained in Example 14.

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours
  2. concentrationconcentrated by evaporation under reduced pressure
  3. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7e4a235f7bf04b8a8b320af81373770d
Source dataset
uspto-grants-2008_11
Patent number
US07449580B2

Linked notes

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