Ethylene Glycol → HCID 118113438, compound

HRID 1485106Notes

Reaction equation

HRID 1485106 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([CH:13]=[O:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.[CH2:17](O)[CH2:18][OH:19].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[N:11][C:10]([CH:13]3[O:19][CH2:18][CH2:17][O:14]3)=[CH:9][N:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118113157HCID 118113157, compound

Product 1

HCID 118113438HCID 118113438, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution in toluene (20 mL) of the compound (1.66 g) obtained in step (1) above, ethylene glycol (1.11 g) and p-toluenesulfonic acid monohydrate (56.6 mg) were added and, thereafter, the mixture was stirred at 140° C. for an hour using a Dean-Stark apparatus. After cooling the reaction mixture to room temperature, a saturated aqueous solution of sodium hydrogencarbonate was added to it under cooling with ice and extraction was conducted with ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. Purification by silica gel column chromatography (n-hexane:ethyl acetate=100:0-60:40) gave 2-(4-bromophenoxy)-5-(1,3-dioxolan-2-yl)pyrazine as a colorless solid (1.78 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. temperatureunder cooling with ice and extraction
  3. washThe combined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customPurification by silica gel column chromatography (n-hexane:ethyl acetate=100:0-60:40)

Sources & evidence

ORD record
ord-586cf91e2467480db3927edc9cf81565
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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