p-Toluenesulfonic acid → 6,7-dihydro-5H-thieno[3,2-b]pyran-2-carbaldehyde

HRID 15368Notes

Reaction equation

HRID 15368 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[S:14][C:13]2[CH2:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[S:14]1[C:13]2[CH2:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[C:6]1[CH:2]=[O:1]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 574869122-(1,3-dioxolan-2-yl)-6,7-dihydro-5H-thieno[3,2-b]pyran

Product 1

HCID 574869136,7-dihydro-5H-thieno[3,2-b]pyran-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 180AcetoneSolvent

Procedure

2-(1,3-Dioxolan-2-yl)-6,7-dihydro-5H-thieno[3,2-b]pyran (0.48 g, 2.24 mmol) was dissolved in acetone (25 ml) and water (25 drops) and stirred with polystyrene-sulfonic acid resin (MP-TsOH, Argonaut Technologies inc, 1.35 mmol/g, 200 mg, 0.27 mmol) overnight. The reaction mixture was filtered, the filtrate evaporated and azeotroped with toluene. The title compound was obtained as a pale orange oil (0.44 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. customazeotroped with toluene

Sources & evidence

ORD record
ord-2603c295c6774fb2b21832e07be7eeeb
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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