Benzyl Alcohol → 2-(benzyloxy)-6-chloropyrazine

HRID 1709701Notes

Reaction equation

HRID 1709701 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1.O>C1C=CC=CC=1>[CH2:1]([O:8][C:14]1[CH:15]=[N:16][CH:17]=[C:12]([Cl:11])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 785042,6-Dichloropyrazine

Product 1

HCID 117461652-(benzyloxy)-6-chloropyrazineYield 86.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

7.6 g of benzylalcohol was dissolved in 65 ml of benzene, and 2.8 g of 60% sodium hydride was added little by little to the solution under stirring not so as to foam too much at room temperature. After the addition, stirring was continued for 10 min. at room temperature, followed by reflux for 1 hour. Subsequently, the solution was cooled to 50° to 60° C., and added dropwise with a solution of 10 g of 2,6-dichloropyrazine in 65 ml of benzene for 10 min. Then, after reflux for 4 hours, the reaction was finished. After cooling below 10° C., about 100 ml of water was added, and the separated benzene layer was collected. The residue obtained by distilling off the solvent was purified by silica-gel column chromatography (developing solvent: n-hexane and ethyl acetate) to obtain 12.8 g of 2-benzyloxy-6-chloropyrazine as a colourless oil (yield: 86.5%) nD25 1.5818.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureby reflux for 1 hour
  4. temperatureSubsequently, the solution was cooled to 50° to 60° C.
  5. temperatureThen, after reflux for 4 hours
  6. temperatureAfter cooling below 10° C.
  7. customthe separated benzene layer was collected
  8. customThe residue obtained
  9. distillationby distilling off the solvent
  10. customwas purified by silica-gel column chromatography (developing solvent: n-hexane and ethyl acetate)

Sources & evidence

ORD record
ord-28545ebfaa664ee0983592c789955f6d
Source dataset
uspto-grants-1990_08
Patent number
US04950679

Reaction notes

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