Ethylene Glycol → 2-(3-Thienyl)-1,3-dioxolane

HRID 1877232Notes

Reaction equation

HRID 1877232 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:10][CH2:9][CH2:8][O:7]2)=[CH:2]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 681353-ThiophenecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 3156302-(3-Thienyl)-1,3-dioxolaneYield 96%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of thiophene-3-carbaldehyde (25.0 g), ethylene glycol (18.7 mL) and toluene (250 mL) was added p-toluenesulfonic acid monohydrate (2.13 g), and the mixture was stirred with heated under reflux for 7 hr while dehydrating using Dean-Stark (Dean-Stark) apparatus. Triethylamine (3.11 mL) was added to quench the reaction, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane) to give the title compound (33.6 g, 96%) as a dark brown oil.

Workup

  1. temperaturewith heated
  2. temperatureunder reflux for 7 hr
  3. customto quench
  4. customthe reaction, saturated aqueous sodium hydrogen carbonate solution
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d4681dd0de764def8468e302e8e03239
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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