Ethylene Glycol → 2-(Benzo[b]thiophen-5-yl)-1,3-dioxolane

HRID 501800Notes

Reaction equation

HRID 501800 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[O:14][CH2:13][CH2:12][O:11]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 139097Benzo(b)thiophene-5-carboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 139229092-(Benzo[b]thiophen-5-yl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

16.5 g of 1-benzothiophene-5-carbaldehyde and 49.5 mL of ethylene glycol were dissolved in 165 mL of toluene, to which 0.30 g of para-toluenesulfonic acid monohydrate was added, and this solution was stirred for 7 hours while heating it under reflux. The reaction mixture was cooled to room temperature, to which an aqueous solution of sodium hydroxide was added, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 15.8 g of 2-(1-benzothiophen-5-yl)-1,3-dioxolane as yellow oil.

Workup

  1. additionwas added
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. additionwas added
  5. customthe organic phase was separated
  6. washAfter the resultant organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled out under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-683404479e084cfea842fab3972bba9e
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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