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

HRID 1071626Notes

Reaction equation

HRID 1071626 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].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1(C)C=CC=CC=1>[O:7]1[CH2:8][CH2:9][O:10][CH:6]1[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 681353-ThiophenecarboxaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 3156302-(3-Thienyl)-1,3-dioxolaneYield 86.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.3 g (181 mmol) of 3-thiophenealdehyde, 50 ml of ethylene glycol and 2.00 g (7.96 mmol) of PPTS were dissolved in 230 ml of toluene, and dehydration was carried out using Dean-stark. After completion of the reaction, the mixture was extracted with ethyl acetate. The extract was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give a crude product. The crude product was subjected to silica gel (ethyl acetate:hexane=1:10), to give 12.1 g (77.3 mmol, 86.7%) of the title compound as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-d3dae8f51af5425e89ab554825f72d96
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

Loading…