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

HRID 2209203Notes

Reaction equation

HRID 2209203 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14](Cl)[N:13]=1>C1COCC1>[CH2:3]([O:10][C:14]1[CH:15]=[N:16][CH:17]=[C:12]([Cl:11])[N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

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

Product 1

HCID 117461652-(benzyloxy)-6-chloropyrazineYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled mixture of sodium hydride (60%, 300 mg, 7.5 mmol) in THF (20 mL) at 0° C. was added dropwise benzyl alcohol (0.75 mL, 7.24 mmol). After 30 minutes, 2,6-dichloropyrazine (999 mg, 6.71 mmol) was added and mixture was warmed to room temperature and stirred overnight. After quenching with sat. NH4Cl(aq), mixture was extracted with ethyl acetate and combined organics were washed with water then brine. Organics were dried, filtered, and concentrated under reduce pressure to yield 2-(benzyloxy)-6-chloropyrazine 5.33 (1.45 g), which was used in the next step without further purification.

Workup

  1. customAfter quenching with sat. NH4Cl(aq), mixture
  2. extractionwas extracted with ethyl acetate
  3. washcombined organics were washed with water
  4. customOrganics were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f229db5c00dc466cb9c4fe13087bb213
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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