Allyl Alcohol → 2-Chloro-3-[(prop-2-en-1-yl)oxy]pyrazine

HRID 1701740Notes

Reaction equation

HRID 1701740 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH2:9]([OH:12])[CH:10]=[CH2:11].[H-].[Na+]>CS(C)=O>[CH2:9]([O:12][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1)[CH:10]=[CH2:11]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 785752,3-Dichloropyrazine

Product 1

HCID 136828382-Chloro-3-[(prop-2-en-1-yl)oxy]pyrazine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

59.6 g of 2,3-dichloropyrazine and 92.8 g of allyl alcohol are dissolved in 400 ml of dimethylsulphoxide. 9.6 g of sodium hydride are introduced into this solution over the course of 30 minutes at 0°-5° C., whilst stirring. The mixture is then stirred for 15 hours at room temperature. Thereafter the reaction mixture is poured into 2 liters of ice water and extracted by shaking with ether. The ether extracts are washed with water, dried over sodium sulphate and evaporated in a waterpump vacuum. The residue is distilled in a high vacuum. 2-Allyloxy-3-chloro-pyrazine, boiling point 42°-44° C./0.03 mm Hg, is thus obtained.

Workup

  1. stirringThe mixture is then stirred for 15 hours at room temperature
  2. extractionextracted
  3. stirringby shaking with ether
  4. washThe ether extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in a waterpump vacuum
  7. distillationThe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-ae20242a2ece4a3993ee0974b4a10122
Source dataset
uspto-grants-1980_03
Patent number
US04195090

Reaction notes

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