Ethylene Glycol → 2-(3-Bromothiophen-2-yl)-1,3-dioxolane

HRID 1418097Notes

Reaction equation

HRID 1418097 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[CH2:9](O)[CH2:10][OH:11].C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]1[O:11][CH2:10][CH2:9][O:8]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 27970793-Bromothiophene-2-carboxaldehyde

Product 1

HCID 122202112-(3-Bromothiophen-2-yl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-bromo-2-formylthiophene (3.89 parts, 0.02M) was heated at reflux with dry ethyleneglycol (1.6 parts) toluene (25 parts) and p-toluene sulphonic acid (0.1 parts) in a vessel equipped with a Dean and Stark separator for 16 hours. The reactants were then cooled and evaporated into silica. The silica was formed into a column which was then developed by elution with hexane containing increasing amounts of dichloromethane. The product was obtained from fractions containing 10-60% dichloromethane as a pale straw-coloured oil (4.42 parts).

Workup

  1. customequipped with a Dean and Stark
  2. temperatureThe reactants were then cooled
  3. customevaporated into silica
  4. customThe silica was formed into a column which
  5. washwas then developed by elution with hexane containing
  6. temperatureincreasing amounts of dichloromethane
  7. customThe product was obtained from fractions

Sources & evidence

ORD record
ord-9a42a9db6fe040e7a8af27860342855a
Source dataset
uspto-grants-1999_03
Patent number
US05880188

Reaction notes

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