Ethylene Glycol → 2-Ethyl-2-2-thienyl-[1,3]dioxolane

HRID 49326Notes

Reaction equation

HRID 49326 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:9])[CH2:7][CH3:8].C[Si](Cl)(C)C.[CH2:15](O)[CH2:16][OH:17]>>[CH2:7]([C:6]1([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[O:17][CH2:16][CH2:15][O:9]1)[CH3:8]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6397ChlorotrimethylsilaneHCID 261792-Propionylthiophene

Product 1

HCID 179347502-Ethyl-2-2-thienyl-[1,3]dioxolane

Procedure

30 g (214.3 mmol) of 1-2-thienyl-1-propanone are dissolved in 120 mL of ethylene glycol. 93 g (856 mmol) of trimethylsilyl chloride are then added. The reaction medium is stirred at room temperature for 24 hours. After treatment with water, the medium is extracted with ethyl acetate and the organic phases are then combined, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica (eluent: 90 heptane/10 ethyl acetate). A yellow oil is obtained (m=15 g; Y=38%).

Workup

  1. extractionAfter treatment with water, the medium is extracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified by chromatography on a column of silica (eluent: 90 heptane/10 ethyl acetate)
  6. customA yellow oil is obtained (m=15 g; Y=38%)

Sources & evidence

ORD record
ord-3f22a21e5d8f4203a92994a228ef1806
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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