Ethylene Glycol → HCID 19434044, compound

HRID 1736037Notes

Reaction equation

HRID 1736037 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[CH:8]=[O:9].[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[CH:8]1[O:12][CH2:11][CH2:10][O:9]1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 8190403,5-dibromothiophene-2-carbaldehyde

Product 1

HCID 19434044HCID 19434044, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture consisting of the product from Step A (11.0 g, 40.7 mmol), TsOH (0.25 g) and ethylene glycol (5.06 g, 81.5 mmol) in toluene (150 mL) was heated at reflux temperature for 1.5 h, water was removed by a Dean-Stark trap. The reaction mixture was cooled and poured into a saturared aqueous solution of sodium bicarbonate (100 mL). The organic layer was separated, dried (MgSO4), and evaporated to dryness. Purification of this crude material by column chromatography (silica, 6% ethyl acetate/hexane) gave 10.33 g of an oil (81%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1.5 h
  3. customwater was removed by a Dean-Stark trap
  4. temperatureThe reaction mixture was cooled
  5. additionpoured into a saturared aqueous solution of sodium bicarbonate (100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customPurification of this crude material by column chromatography (silica, 6% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d264e1dad26489098f8308b37e4c13c
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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