1-Hexanol → HCID 22413523, compound

HRID 1721615Notes

Reaction equation

HRID 1721615 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[Cl:10][C:11]1[C:16](Cl)=[N:15][CH:14]=[CH:13][N:12]=1>C1COCC1>[Cl:10][C:11]1[C:16]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:15][CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 785752,3-Dichloropyrazine

Product 1

HCID 22413523HCID 22413523, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

Hexanol was added to a slurry of sodium hydride in THF, and the mixture stirred for 30 minutes. The slurry was cooled to -5° C. and a solution of 2,3-dichloropyrazine added. The mixture was stirred for 1.5 hours, filtered and the filtrate evaporated. The residue was purified by column chromatography on silica gel using varying concentrations of methanol in chloroform. Fractions containing the desired product were evaporated, yielding 2-chloro-3-hexyloxypyrazine as an oil.

Workup

  1. stirringThe mixture was stirred for 1.5 hours
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. customThe residue was purified by column chromatography on silica gel using
  5. additionFractions containing the desired product
  6. customwere evaporated

Sources & evidence

ORD record
ord-997183ad4a654af3b34e9a4a56453bc0
Source dataset
uspto-grants-1996_04
Patent number
US05512574

Reaction notes

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